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IDENTIFICATION OF ESSENTIAL OIL COMPONENTS BY GAS CHROMATOGRAPHY/ MASS SPECTROMETRY, ed. 4.1 Dr. ROBERT P. ADAMS Professor Biology Department Baylor University



ed. 4.1, 30 Jan. 2017



Neither this book nor any part may be reproduced or transmitted in any from by any means, electronic or mechanical, including photocopying, microfilming and recording, or by any information storage retrieval system without the permission in writing from the publisher. an electronic version of the original 4th ed. printed by Allured publishing, 2007 ed. 4.1, 30 Jan. 2017 ISBN 978-1-932633-21-4



CONTENTS Preface



v PART A GAS CHROMATOGRAPH/MASS SPECTROSCOPY



I Introduction II. Nomenclature III. Mass Spectrometry Considerations A. Obtaining Quality Spectra for Identification B. The Role of Retention Times in Library Searches IV. Operating Conditions Used for Spectra Acquisition V. Compatibility with Mass Spectrometer Data Systems VI. Explanations of Formats Used in Appendices VII. References



1 1 2 2 3 4 5 6 7



PART B APPENDICES I II III IV



Alphabetical Listing of Compounds with Their Retention Time and Arithmetic Retention Index on DB-5 Compounds Listed in Order of Their Retention Time and Arithmetic Index on DB-5 Mass Spectra and Structures of Compounds Listed in Order of Their Retention Time/Arithmetic Index on DB-5 Cross Index of Common Names



9 31 53 698



iii



Preface This is the fourth edition on mass spectra and retention times of common components in plant essential oils. It differs from the previous in edition in that an additional 600 compounds have been added and the source of the sample has been added, along with a few sources in nature for most of the compounds. All of the compounds have been analyzed on an HP5970 MSD mass spectrometer using HP Chemstation software. I hope it will be a useful as a tool for the identification of compounds in this format. In addition, the library (including retention times) is available for the most common mass spectrometer/ computer systems. Changes in technology allow us to make this available now. For instance, when I began research on essential oils in 1966, a major portion of my thesis work involved the identification of components in Juniperus by IR spectra. Of course that involved cold trapping compounds as they eluted from the TC detector on GC. With current mass spectrometers, we can now accomplish in a couple of hours the analysis that took months or years. This book is an outgrowth of the previous books (Identification of Essential Oils by Ion Trap Mass Spectroscopy, Academic Press, 1989; Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy, Allured Publishing, 1995), but its roots reach back to 1976 when I took a sabbatical study with Ernst von Rudloff and Lawrence Hogge at the National Research Council of Canada. Our collaborative efforts yielded numerous mass spectra on their quadrupole mass spectrometer. Later, as I visited with colleagues in chemical ecology, I began to appreciate the library that I had assembled. So this book is an outgrowth of much collaboration, starting with Ernst von Rudloff and now reaching around the world. I owe a special debt of thanks to colleagues who unselfishly sent samples of oils, mass spectra, marked chromatograms, and even purified compounds. These colleagues include: E. A. Aboutabl, Egypt; Aldrich Chemical Co., USA; J. Altarjos, Spain; Applied Science Co., USA; A. Badoc, France; A; J. Barroso, Portugal; K. H.C. Baser, Turkey; A. F. Barrero, Spain; J. Berlin, Germany; H. Bussenius, Haiti; J. J. Brophy, Australia; E.-J. Brunke, Symrise GmbH & Co. (formerly Dragoco), Germany; J. L. R. Canavate, Spain; R. M. Carman, Australia; J. Casanova, France; F. M. Chaudary, Pakistan; T. S. Chamblee, Coca Cola Co., USA; A. Chainteau, Nestec, Switzerland; J. C. Chalchat, France; M. Chien, Givaudan, USA; G. Collin, Canada; D. Clark, New Zealand; L. Cool, USA; A. Cornat, France; A. A. Craveiro, Brazil; W. Cretney, Canada; R. Croteau, USA; Jian-Qin Cu, China; C. Demetzos, Greece; H. De Pooter, Belgium; M. Deyrup, USA; V. Dev, USA; R. P. Doss, USA; V. Dragar, Australia; G. Dugo, Italy; L. Doimo, Australia; F. S. El-Feraly, Saudi Arabia; G. Elzen, USA; W. W. Epstein, USA; N. Fisher, Germany; R. Estell, USA; Z. Fleisher, Crompton & Knowles, USA; C. Franz, France; R. P. Garry, France; S. Geribaldi, France; K. Gollnick, Germany; J. Hafizouglu, Turkey; K. J. Harkiss, England; C. Harvala, Greece; S. Hasegawa, Japan; A. R. Hayman, New Zealand; E. Hethelyi, Hungary; H. G. Hills, USA; J. Hendrickson, USA; L. Hogge, Canada; G. Honda, Japan; M. Ito, Japan; P. Joseph-Nathan, Mexico; D. Joulain, France; A. J. Kahn, USA; W. A. Konig, Germany; S. Kral, IFF, USA; J. Langenheim, USA; D. Lamparsky, Givaudan, Switzerland; A. Lara, Spain; B. M. Lawrence, USA; N. G. Lewis, USA; M. Maffei, Italy; M. L. Maheshwari, India; C. S. Mathela, India; C. A. McDaniel, USA; B.Y. Meklati, Algeria; A. Michet, France; C. Menut, France; L. N. Mishra, India; D. McMahon, Union Carbide Corp., USA; K. Moriai, Japan; M. G. Moshonas, USA; R. D. H. Murray, Scotland; S. Nagahama, Japan; K. R. Neisess, USA; I. Nykanen, Finland; J. Oda, Japan; T. H. Ohaski, Japan; S. Park, USA; F. Perineau, France; W. Phillips, USA; G. Prestwich, USA; R. A. Raguso, USA; P. Raharivelomanana, France; P. Richomme, France; B. Rodriguez, Spain; V. Roussis, Greece; A. San Feliciano, Spain; J. J. C. Scheffer, Netherlands; R. Scheffrahn, USA; G. Schmaus, Symrise GmbH & Co. (formerly Dragoco), Germany; N. Sellier, France; D. Senalik,USA; S. Shatar, Mongolia; H. Shiota, Japan; E. Silva, Mexico; I. Southwell, Australia; E. Stahl-Biskup, Germany; R. Stipanovic, USA; A. B. Svendsen, Netherlands; A. Tara, Italy; A. Tenaglia, France; R. S. Thakur, India; R. K. Thappa, India; A. F. Thomas, Firmenich, Switzerland; M. Toyoat, Japan; R. R. Trenkle, IFF, USA; A. O. Tucker, USA; A. Ulubelen, Turkey; T. A. van Beek, Netherlands; A. Velasco-Negueruela, Spain; J. P. Vidal, France; O. Vostrowsky, Germany; G. J. Wagner, USA; P. Waterman, U.K.; R. Weavers, New Zealand; H. Weyerstahl, Germany; P. Weyerstahl, Germany; P. T. White, USA; M. Whitten, USA; H. J. Woerdenbag, Netherlands; K. C. Wong, Malaysia; Xu JiQing, China; Xiaobing Yu, China; P. Yates, Canada; Y. Yuesa, Japan; T. A. Zanoni, USA; M. G. B. Zoghbi, Brazil; J. A. Zygadlo, Argentina; and J. H. Zwaving, Netherlands. Special thanks Maarten Posthumus who faithfully sent me typo and structural errors from previous editions and printings. His keen eyes and cooperative spirit have been important in producing this book. iv



Thanks to Tonya Yanke, Lou Garrett, Madeline Reed and Ryan Perez for assistance with word processing and drawing structures. Also thanks to several young students who helped: Carlos Borunda, Blake Fitzgerald and Ryan Remick. Finally, I would like to thank my wife, Janice, for her patience and encouragement.



v



PART A COMBINED GAS CHROMATOGRAPHY/ MASS SPECTROMETRY I. INTRODUCTION The utilization of essential oils of plants is widespread ranging from perfumes and fragrances, to spices and medicinals. Research has varied from very applied, as in the case of quality control of fruit juices, to academic studies involving insectplant coevolution. But in all cases, the investigator or user is faced with the problem of identification of numerous components in generally very complex mixtures. The volatile (usually taken to mean steam distillable) plant oils are composed of chiefly terpenoids: mono-, sesqui- and di-terpenes, plus various alcohol, ketone and aldehydes of terpenoids, with frequently occurring aromatic compounds arising from the phenyl-propanoid pathway (i.e., eugenol, safrole, elemicin, etc.). In some species, one may obtain alkanes and aliphatic alcohols, ketones and aldehydes. Many of the components of plant essential oils are common to many species (i.e., -pinene, limonene, myrcene, camphor, etc.). In fact, it appears that the ability to identify perhaps as few as five hundred compounds would enable one to identify more than 90% of the constituents of the essential oil of most species. Of course, there are exceptions such as Artemesia (Epstein, et al., 1976) with its non-head-to-tail monoterpenes. But, one only has to examine the works of Craveiro, et al. (1981), Formacek and Kubeczka (1982), Lawrence (1978, 1979), and Masada (1976) to see the reports of a few hundred compounds from hundreds of species. Even though most of the identifications encountered in essential oils (and particularly physiological analyses of seasonal and edaphic factors in commercial spice and essential crops) may involve common terpenoids, unequivocal identification can be difficult (Adams, et al., 1979). Historically, essential oil components have been identified by infrared spectroscopy (IR) with stereochemistry assigned by nuclear magnetic resonance (NMR). Only rarely has ultraviolet spectroscopy (UV) been useful for identification. Although liquid phase IR is very explicit (essentially fingerprints) for most components, the difficulty in isolation of pure fractions containing only a single minor component has largely negated the present use of liquid phase IR. The development of vapor phase IR and the concurrent construction of reference libraries might expand the use of vapor phase IR for the identification of essential oils. The advent of fused quartz, bonded-phase capillary columns has led to very reproducible retention times and reproducible columns from batch to batch (Jennings, 1987). Given reproducible retention times, the unequivocal identification of essential oil components is possible by retention time/ mass spectrometry/ computer searching algorithms (Adams, et al., 1979; Adams, 1989; 1995; 2001). The introductions of the Ion Trap Detector (ITD) or ion trap mass spectrometry by Finnigan Corp. and the desktop quadrupole by Hewlett-Packard, to name but two, have made available relatively inexpensive mass spectrometers that have full computer searching capabilities. In addition, users can build their own library and search them. The purposes of this book are to present quadrupole mass spectra, retention times, structures, and synonymy for the most commonly occurring plant essential oil components. II. NOMENCLATURE There no general agreement on the nomenclature of common names utilized for essential oil components. Because of the long historical usage of common names, the more precise chemical names provided by the Chemical Abstract Service (CAS) are seldom used. However, there are some conventions that need to be adopted for the common names that will lead to more uniformity. It has been common to call isomers about a double bond as cis and trans rather than E and Z (below): E



'trans'- hex-3-enol



OH



Z



OH



'cis'-hex-3-enol



1 However, in this book, I shall try to be consistent in naming all double bond isomers as E or Z, not trans or cis. So the hexenol above, will be called (3E)-hexenol and (3Z)-hexenol not trans-hexenol or cis-hexenol. The nomenclatural situation gets more complicated with ringed compounds such as 'beta-caryophyllene' i.e., (E)-caryophyllene and (Z)caryophyllene:



E



H



H



Z



H H



(E)-caryophyllene



(Z)-caryophyllene



Adams: Essential Oil Components by GC/MS



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Even more confusing for (E)-caryophyllene ('beta-caryophyllene'), the double bond in the alpha position results in the name of alpha-caryophyllene, but this compound is universally called alpha-humulene! True cis and trans- isomers have also resulted in problems. Decouzon et al. (1990) have proposed a system of naming that is often followed (and will be followed in this book). They present the following isomers of menthol:



OH



neomenthol



OH



OH



neoisomenthol



menthol



OH



isomenthol



The naming convention of Decouzon et al. (1990) is used in this book for these kinds of neo-, iso- and neoiso- isomers.



III. MASS SPECTROMETRY CONSIDERATIONS A. Obtaining Quality Spectra for Identification Although operation of the HP mass selective detector (MSD) and other desktop mass spectrometers is automatic in most aspects, there are a number of areas in which the user needs to be careful in choosing a spectrum for identification. Obviously the choice of a column, its installation and use are very important in obtaining separation, to eliminate bleed, etc. Because Jennings (1987) has published an excellent treatise on capillary column gas chromatography, the reader is referred to that book for detailed discussion of capillary gas chromatography. The HP MSD can be tuned using either an "Automatic Tune" or a "Target Tune". The use of "Autotune" should be avoided, because the 'Target Tune" gives more consistent mass spectra over a time period. Our HP MSD was tuned using “Target Tune”, with target tune values of M69 100%; 1313 - 40%, 219 - 64%, 502 - 3%. In figure 1, one can see the Automatic Tune Figure 1. Comparison of Automatic Tune vs. Target Tune spectra. (upper) and Target Tune (lower). Notice the much larger amount of M219, Fig. 1 and some increase in M131. Because the essential oil components are often of mass 136 to 222, increasing the ion intensities in this range is very useful. It is important to do a Target Tune any time one cleans the MSD or changes gas cylinders. Oxygen and water can severely affect the mass spectrometer both in the quality of spectra obtained and in permanent damage to components such as the filament. Leak checking should be a daily operation! One should never turn on the filaments before doing a leak check. One should also run a standard (ex. cedrol) each week to determine if any changes in tuning have occurred. When the mass spectrometer is turned off for cleaning or repair, a complete recalibration should be done, starting first with a leak check for air and water. Because even the bonded phase polar columns are degraded by oxygen and water, high quality helium (or hydrogen) should be used and both oxygen and water traps should be inserted between the supply cylinders and gas chromatograph. No other aspect is consistently so troublesome as overloaded spectra. One should be very careful with large peaks to avoid overloaded spectra. As a general rule, the spectra in this book were chosen either at the mid-point for small peaks or at about 0.05 min. from the start of the peak for large peaks. Please note: The retention times are NOT at the center for large peaks! On the system used for this book, small peaks averaged about 0.1 min in width or about 0.05 min to the top of the peak. To be consistent, the retention times for peaks that were larger than 0.1 min wide, were set to 0.05 min past the start of the peak.



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B. The Role of Retention Times in Library Searches Because unequivocal identification of some terpenoids can not by made on the basis of their mass spectra (with current technology), the use of retention times is critical. As of this date, most data systems do not incorporate retention times in their library searches. For this reason, I have included the retention time just before the name for each compound in the library (ex. 5.62 thujene ). Thus, 5.62 is the retention time in mins. on DB-5, 30 m, temperature programmed from 60 oC to 246 oC at 3 oC /min. ramp. Figure 2 shows the result of a library search for the compound at 5.589 to 5.647 in lemon oil. For this small peak, I would use a RT of 5.589 min. + 0.05 min. = 5.639 min. This closely matches the RT for the first match (5.62 thujene



Figure 2. Library search for -thujene from lemon oil (top) vs. -thujene from the library. Notice that the second match was to -phellandrene at nearly the same quality level (94 vs. 91). from the HP Chemstation search. Although the second match (7.85 phellandrene (alpha->) is nearly as similar, note that the retention time (7.85 min.) is far too late to be the unknown peak. A second example (Fig. 3) shows the searching for a large compound in lemon oil. In this case, the scan through the peak is from 8.657 to 8.865. So I would round up the last digit (8.657 -> 8.66 and add 0.05 min = 8.71. The HPChemstation search correctly identified the peak as limonene (Fig. 3), with a RT in the library of 8.69 min. In general, you should expect to be within 0.1 min. of the library time if you use the same DB-5, 30m column, same temperature ramp (60 oC to 246 oC at 3 oC /min. and if you correct your peaks RT to library values when you identify new peaks. We routinely add two internal standards to our samples: octane (C8) and eicosane (C20). If the starting time is incorrect, a correction can be added to the early peak's retention times. If some problem has developed in the gas chromatograph's oven temperature controller and/or column characteristics, this changes the retention time of eicosane. In actual practice, you can easily adjust retention times as you process the output by merely noting the retention time (RT) of major peaks that are easily identified and then either adding or subtracting the difference in their RT and that in the library. For example, if in the above example, -thujene in lemon oil had a RT of 5.50 versus 5.62 in the library, then I would begin to add 0.12 min to the RT of the next peak(s). If further along in the chromatogram, geraniol had a RT of 17.81 versus 17.95 in the library, then I would begin adding 0.14 min. to the RT of the next peak(s). By adjusting the RT as one “crawls” along the chromatogram, one can attain very good retention times. It should also be noted that occasionally, the library search just does not seem to pick up some subtle differences and it is useful to have the book opened to about the unknown’s RT and just look on the pages! Our eyes are still pretty good at seeing patterns that computer searches miss.



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Figure 3. Library search for unknown and match to library Limonene.



IV. OPERATING CONDITIONS USED FOR SPECTRA ACQUISITION Mass spectra were obtained on an Hewlett Packard (HP) model 5970b MSD mass spectrometer, coupled directly to a HP 5890 gas chromatograph fitted with a J & W DB-5, 0.25 mm i.d. x 30 m, 0.25 micron coating thickness, fused silica capillary column. The GC/MSD was operated under the following conditions: injector temperature - 220 oC; transfer line - 240 oC; oven temperature programmed - 60 oC to 246 oC @ 3 oC/min; carrier gas - He @ 34.96 cm/sec or 1.02 ml/min (@ 210 oC); injection (for most whole essential oils) - 0.1 µl (10% soln.), split 1:20, 500 ng/on column; (for individual or simple mixtures of reference compounds) - 0.1 µl (1% soln.), split 1:20, 50 ng/on column. Internal standards (n-octane and n-eicosane) were added to each sample to aid in the standardization of retention times. The following is a typical set of values for our instrument: EM Volts 1800v., X ray 44.0, emission on, Amu Gain 88, Amu Offs 60, Mass Gain 52, Mass Offs 14, Repeller 10.20, Ion Focus 0.0, Ent Lens 54. Acq. Mode Scan, Scan Range 41 415, 1 scan/ sec., Solvent delay 2.00 min., V. COMPATIBILTY WITH MASS SPECTROMETER DATA SYSTEMS In addition to this printed book, a computer searchable library is available for use on the following systems: 1. Palisade Bench Top/PBM, (PBM2205.SPC) 2. Finnigan GCQ/ (GCQM2205.LBR) 3. VARIAN SATURN (VARS2205.LBR) 4. Finnigan Ion Trap, (ITD2205.LIB & ITD2205.INX ) 5. Finnigan INCOS (FINC2205.LS & FINC2205.LX) 6. Fisons/VG JCAMP (FISV2205.JDX) 7. Fisons/VG Mass Lab(FIML2205.IDB,.IDI,.PDB,&.PDI) 8. HP JCAMP, Unix (HPJC2205.HPJ) 9. HP CHEMSTATION [Dir \HPCH2205.L, plus 7 files: ROOT; HEADER; HEADER.IND; CAS.IND; CONDENSE; CONDENSE.IND; FULL.D] 10. net CDF (NETC2205.CDF) 11. PE Turbomass (PETU2205.IDB,.IDI,.PDB,& PDI) 12. Shimadzu QP5000 (6 files: SHIM2205.NAM, .FOM, .LIB, .SPC, .COM, .FLG) 13. MassFinder (MF32205.mfl) [14.] Finnigan Triple Quad can automatically convert the .LS, .LX (#5. above) formatted library. [15.] Finnigan ICIS can read Finnigan Ion Trap(.LIB, .INX, #4. above) formatted library



Adams: Essential Oil Components by GC/MS



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[16.] Teknivent Vector 2 can read PBM (#1. above) formatted library [17.] NIST format, this library can be created by converting HP Chemstation (9. above) using LIB2NIST.exe that is a free download from http://chemdata.nist.gov. Many of the data systems can input a HP Jcamp (8.) formatted library and convert it to their internal format. It should be noted that 13 (above) Mass Finder is a stand alone software that can input mass spectral data from most systems. MassFinder can be used to process and identify compounds using a combination spectral data and retention times.



Figure 4. MassFinder search page showing the identification of -cadinene. The middle section displays the previous, current, and next scan from the RIC (left). Library matches are on the right side, ranked by similarity (1 and 2 of 27 shown). Figure 4 shows a search from MassFinder. One of the benefits of Mass Finder is that it displays the previous and next mass spectral scan as well as the current scan. So it is easy to detect mixed peaks. Another very useful feature of MassFinder is the capability of outputting customized RIC and mass spectra from publication. Information on MassFinder is available from Detlev Hochmuth at www.massfinder.com. VI. EXPLANATIONS OF FORMATS USED IN APPENDICES Because retention times may vary as columns age and if different carrier gases are used, it is useful to have an index based on a series of standards, such as straight chain hydrocarbons. The most common index is the Kovats Index (Kovats, 1965). Kovats Indices are computed using formula (2), p. 230 from Kovats (1965) as follows: KI (x) = 100 Pz + 100 [(log RT (x) - log RT (Pz )) / (log RT (Pz+1 ) - log RT (Pz ))] Where: RT (Pz)  RT(x)  RT(Pz+1 ), and P4 ... P34 are n-paraffins. (up to N=34 in this book).



Adams: Essential Oil Components by GC/MS



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However, Van den Dool and Kratz (1963) noted earlier that when temperature programming is done, an arithmetic index (AI) would be more appropriate than a logarithm based index. The Arithmetic Index used in this edition was computed as: AI (x) = 100 Pz + 100 [(RT (x) - RT (Pz )) / (RT (Pz+1 ) - RT (Pz ))] Both AI and KI indices are presented for each compound in Appendix III. The first appendix presents an alphabetical list of the compounds for which mass spectra were obtained and includes their retention time and Arithmetic Index on a J & W DB-5, 30 m, 0.26 mm i.d., 0.25 micron coating thickness, with helium carrier gas at 31.9 cm/sec (1.017 ml/min), programmed temperature of 60 to 246 oC at 3 oC/min. The problem of presenting different retention indices has been discussed by Jennings (1978) and Jennings and Shibamoto (1980). I have chosen to follow Jennings and Shibamoto (1980) in publishing retention times but have also included both Arithmetic and Kovats Indices. A small DOS program (ARITHIND.EXE) is included on the CD ROM that may be used to print out a complete table of RTs, AIs and KIs from RT = 1.43 to 82.80 minutes (C4 - C34 alkanes). It should be noted that retention on a carbowax type column may seem essential, but we have found even bonded carbowax to change polarity characteristics rather quickly (and therefore change the retention times) . The non-polar phases lack some of the resolving power for alcohols and ketones, but the longer term stability and lower batch-to-batch variability offset that liability. The polarity of a DB-5 column is equivalent to: BP-5, CP-SIL-8CB, DC-200, DC-560, Dexsil 300, GB5, OV-3, OV-73, SE-52, SE-54, SPB-5, Ultra 2, and 007-2. Appendix II lists the compounds by retention times on DB-5. This list is useful when you are identifying compounds, as it is a quick guide to see if a library match runs close to the peak you are analyzing. Appendix III presents the quadrupole spectra of compounds that are most commonly encountered in the identification of essential oils. Unfortunately, several very common compounds are not in the appendix because we could not obtain authentic reference compounds. Each of the compounds was searched in Chemical Abstracts Service to obtain the current chemical or systematic name (CN), to supplement registry numbers, to supplement synonyms. Structural information came from original literature sources (see preface), Aldrich Chemical Co. catalog, Alfa Chemical Co. catalog, Chemical Abstracts Service, Devon and Scott (1972), DICTIONARY OF ORGANIC COMPOUNDS (1982), FOOD CHEMICAL CODEX (Dodgen, 1981), EPA/NIH mass spectral data base (Heller and Milne, 1980), Formacek and Kubeczka (1982), Jennings and Shibamoto (1980), Pfaltz and Bauer Chemical Co. catalog, Swigar and Silverstein (1981), von Sydow, Anjou and Karlsson (1970), Masada (1976), Merck Index (Windholz, 1983), and Yukawa (1973). As far as practical, the structural patterns used by Devon and Scott (1972) were followed. Each of the compounds follow the same format: RT.............. AI……KI..... Common name...................................................................... CAS#: ...................... MF:.............. FW:............. MSD Lirb#:........... CN:........................................................................................................................... SYNONYMS:......................................................................................................... SOURCE:…………………………………………………………………………. Where: RT = retention time on DB-5 column, in minutes. AI: = Arithmetic Index on DB-5 in reference to n-alkanes KI = Kovats Index on DB-5 in reference to n-alkanes. Common name = common name generally used (of course some compounds have two or three names that are very widely used, so it is somewhat arbitrary, no matter which name is used herein). As far as possible, the root of the common name is typed first, with modifiers placed afterwards (ex. TERPINENE not α-terpinene). This enables one to sort the names and hopefully will aid the user in finding names. CAS# = Chemical Abstracts Service reference number. Many of the essential oil components have been assigned several CAS#s over the years because of their independent discoveries around the world. Of course, CAS tries to keep the registry up to date. Another problem with the CAS registry numbers is that the optical rotation of essential oil components is difficult to obtain from trace components in complex mixtures. Therefore, most of the reports of species composition do not include information on optical rotation. For example, the sample of calamenene came from a complex oil mixture and a search of CAS revealed both R (+) and S (-) forms have been reported. Therefore, the choosing of a CAS number becomes arbitrary. This also presents a problem for the staff at CAS when they assign registry numbers to compounds in the literature. MF = molecular formula.



Adams: Essential Oil Components by GC/MS



7



FW = formula weight (or molecular weight) in amu. MSD Libr# = HP MSD library entry number (the library is available on CD ROM from Allured Publishing). CN = chemical or systematic name used by Chemical Abstracts Service. Almost all the names are from the 9th chemical index. SYNONYMS = synonyms for the common name. Some of these are various permutations of an older systematic name (ex. 3-methyl -4-heptanone and 4-heptanone, 3-methyl-). Almost all of the synonyms are cross indexed in Appendix IV. To the right of each compound name and paragraph is the structure, and below is the mass spectrum on the HP Mass Selective Detector (MSD). Although most cis- and trans- isomers follow the CAS rules using the groups with the largest molecular weights to assign cis- and trans-, these rules sometimes differ from traditional usage (e.g., cis- and trans-ßterpineol, cis/trans- sabinene hydrates, etc.). As far as possible, the CAS system is followed and noted on the compound entry. SOURCE = source of the compound used for the analysis, plus other natural sources where known. Appendix IV lists all the synonyms and cross-references the synonyms to the common name as an aid for the reader. The accepted common names (used for the spectra in Appendix III) are in bold face capitals (ex. ABIETAL). VI. REFERENCES Adams, R. P. 1970. . Seasonal variation of terpenoid constituents in natural populations of Juniperus pinchotii Sudw. Phytochem. 9:397-402. Adams, R. P. 1989. Identification of Essential Oils by Ion Trap Mass Spectroscopy, Academic Press, San Diego, CA. Adams, R. P. 1995. Identification of Essential Oil Components by Gas Chromatography/ Mass Spectroscopy, Allured Publishing, Carol Stream, IL, USA. Adams, R. P. 2001. Identification of Essential Oil Components by Gas Chromatography/ Quadrupole Mass Spectroscopy, Allured Publishing, Carol Stream, IL, USA. Adams, R. P. and L. Hogge. 1983. Chemosystematic studies of the Caribbean junipers based on their volatile oil. Biochem. Syst. Ecol. 11:85-89. Adams, R. P., M. Granat, E. von Rudloff and L. Hogge. 1979. Identification of lower terpenoids from gas-chromatographmass spectral data by on-line computer method. J. Chromatographic Sci. 17:75-81. Adams, R. P., T.A. Zanoni and L. Hogge. 1985. The volatile leaf oils of the Junipers of Guatemala and Chiapas, Mexico: Juniperus comitana, J. gamboana and J. standleyi. J. Nat. Prod. 48:678-680. Aldrich Chemical Company Catalog. Milwaukee, WS. Craveiro, A. A., A.G. Fernandes, C.H.S. Andrade, F.J.D. Matos, J.W. Alencar and M. I.L. Machado. 1981. Oleos Essenciais de Plantas do Nordeste, Edicoes UFC, Fortaleza, Brazil Decouzon, M., J-F. Gal, S. Geribaldi, M. Rouliard and J-M. Sturla. 1990. Differentiation of diasteroisomeric alcohols by electron impact and negative ion chemical ionization associated with collision-induced dissociation. AFourier transform ion cyclotron resonance study. Organic Mass Spectrometry 25: 312-316. Devon, T. K. and A.I. Scott. 1972. Handbook of Naturally Occurring Compounds. Vol. II. The Terpenes, Academic Press, New York, NY. Dictionary of Organic Compounds. 5th Edition 1982. J. Buchingham, ed., Chapman and Hall, New York, NY. Dodgen, D. F. 1981. Food Chemicals Codex. 3rd Edition, National Academy Press, Washington, DC. Epstein, W. W. and L.A. Gaudioso. 1984. Volatile constituents of sagebrush. Phytochemistry 23: 2257-62. Formacek, V. and K.-H. Kubeczka. 1982. Essential Oils Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy, John Wiley & Sons, New York, NY. Heller, S. R. and G. W. A. Milne. 1980. EPA/NIH Mass Spectral Data Base, U.S. Government Printing Office, Washington, DC. Jennings, W. 1978. Gas Chromatography with Glass Capillary Columns, Academic Press, New York, NY. Jennings, W. 1987. Analytical Gas Chromatography, Academic Press, New York, NY. Jennings, W. and T. Shibamoto. 1980. Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Gas Chromatography, Academic Press, New York, NY. Kovats, E. 1965. The retention index system. pp. 229-247. in Advances in Chromatography, Vol. I., J.C. Giddings and R.A. Keller (eds.), Marcel Dekker, Inc.New York, NY. Lawrence, B. M. 1978. Essential Oils 1976-1977, Allured Publishing Co., Wheaton, IL.



8



Adams: Essential Oil Components by GC/MS



Lawrence, B. M. 1979. Essential Oils 1978, Allured Publishing Co., Wheaton, IL. Masada, Y. 1976. Analysis of Essential Oils by Gas Chromatography and Mass Spectrometry, John Wiley & Sons, Inc., New York, NY. Pfalz and Bauer Chemical Company Catalog. Southwell, I.A. 1987. Essential oil isolates from the Australian Flora. Part 2. Flavor and Frag. J. 2: 21-27. Swigar, A. A. and R.M. Silverstein. 1981. Monoterpenes: Infrared, Mass, 1HNMR and 13C NMR Spectra, and Kovats Indices, Aldrich Chemical Co., Milwaukee, WS. Van den Dool, H. and P. Dec. Kratz. 1963. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatography 11: 463 - 471. von Sydow, E., K. Anjou and G. Karlsson. 1970. Mass Spectral Data of Terpenes, Svensak Institut for Konserveringsforskning Rapport, Nr 279, Kalleback. Windholz, M. (ed.).1983. The Merck Index. 10th Edition, Merck & Co., Inc., Rahway, N.J. Yukawa, Y. and S. Ito, (eds.). 1973. Spectral Atlas of Terpenes and the Related Compounds, Hirokawa Publishing Company, Inc. Tokyo.



PART B APPENDICES



Appendix I ALPHABETICAL LISTING OF COMPOUNDS WITH THEIR RETENTION TIME AND ARITHMETIC RETENTION INDEX ON DB-5



Adams: Essential Oil Components by GC/MS



10



Common Name Abienol Abieta-(8(14),13(15)-diene Abieta-7,13-diene-3-one Abieta-8,12-diene Abietadien-18-ol Abietadiene Abietal Abietal Abietal Abietatriene Abietol Abietol Abietol Abietol Acetanisole Acetonyl acetone Acetophenone Acetophenone Acetophenone Acetophenone Acetoxyelemol Acetoxyeudesman-4α-ol Acetoxyhexane Acetyl pyridine Acetyl thiophene Acetyl-2,5-dimethyl furan Acetylacetophenone Acetylfuran Acetylpyrrole Aciphyllene Acora-2,4(15)-diene Acora-3,7(14)-diene Acoradiene Acoradiene Acoradiene Acoradienol Acorenol Acorenol Acorenone Acorenone B Acorone Acorone Acrolein Adamantanone Agarofuran Agarospirol Ageratochromene Ageratochromene Agglomerone Alaskene Alaskene Allo-cedrol Allo-hedycaryol Alloevodione Allohimachalol



RT 51.98 52.12 56.85 48.03 57.17 50.08 56.87 56.44 55.74 49.08 59.37 57.72 61.15 58.42 19.76 05.48 09.99



AI 2149 2153 2312 2022 2324 2087 2313 2298 2274 2055 2401 2343 2468 2368 1290 0919 1059



36.80 20.11 22.30 14.91 40.14 45.24 06.10 08.83 10.97 10.78 26.47 05.19 09.79 28.89 26.50 24.93 27.73 27.32 27.52 39.03 34.13 34.30 36.45 36.64 41.09 40.83 11.80 20.64 30.79 34.69 35.16 27.18 36.69 29.31 28.75 32.45 32.45 43.34 35.25



1701 1298 1347 1179 1792 1938 0941 1028 1086 1081 1444 0909 1054 1501 1444 1407 1474 1464 1469 1762 1632 1636 1692 1697 1819 1812 1107 1310 1548 1646 1658 1461 1698 1512 1498 1589 1589 1883 1661



Common Name Allyl anthranilate Allyl butanoate Allyl cinnamate Allyl cyclohexyl propanoate Allyl decanoate Allyl heptanoate Allyl hexanoate Allyl isovalerate Allyl nonanoate Allyl octanoate Allyl tiglate Ambersage Ambrinol Ambrinol Ambroxide Amorph-4-ene Amorpha-4,11-diene Amorpha-4,7(11)-dien-8-one



Amorpha-4,7(11)-diene Amorpha-4,7(11)-diene Amorpha-4,7(11)-diene Amorpha-4,7-diene Amorpha-4,9-dien-14-al Amorpha-4,9-dien-2-ol Amorpha-4,9-diene Amorphane Amorphane Amorphene Amorphene Amorphene Amyl acetate Amyl cinnamaldehyde Amyl cinnamaldehyde Amyl cinnamyl alcohol Andro encecalinol Anethole Anethole Angustifolenone Angustione Angustione Anisaldehyde Anisaldehyde Anisaldehyde , dimethylacetal Anisaldehyde, Anisole Anisole Anisole Anisyl acetate Anisyl alcohol Anisyl alcohol Anisyl formate Anisyl methyl ketone Anisyl propanoate Anthranilate Anthranilate



RT 28.89 04.60 30.78 25.61 27.84 14.86 10.72 05.82 23.65 19.22 08.57 18.58 26.26 25.27 38.81 31.70 26.71



AI 1501 0881 1548 1423 1476 1178 1079 0931 1378 1278 1021 1263 1439 1415 1756 1570 1449



46.84 27.97 40.59 39.49



1985 1479 1805 1775



42.55 36.91 36.77 38.78 28.05 27.91 28.13 29.29 28.63 05.25 35.48 34.73 36.06 35.80 19.43 17.96 14.36 23.38 23.80 17.85 17.50 22.93 15.57 05.32 23.74 08.34 25.13 19.31 19.24 21.52 23.75 29.26 25.23 21.72



1861 1704 1700 1755 1481 1478 1483 1511 1495 0911 1667 1647 1682 1675 1282 1249 1167 1372 1381 1247 1239 1361 1195 0913 1380 1015 1412 1280 1278 1330 1380 1510 1414 1334



Appendix I: Alphabetical List of Compounds



Common Name Apiole Apodophylene Apofarnesal Apofarnesal Apofarnesol Apofarnesol Apritone Apritone Arbozol Arbozol Arbusculone Arbusculone Aristolochene Aristolochene Aristolone Aromadendrane Aromadendrene Aromadendrene Aromadendrene Artedouglasia oxide A Artedouglasia oxide B Artedouglasia oxide C Artedouglasia oxide D Artemiseole Artemisia alcohol Artemisia ketone Artemisia triene Artemisyl acetate Asaricin Asarone Asarone Asarone Ascaridole glycol Ascaridole Atlantol Atlantone Atlantone Atlantone Atlantone Atlantone Atractylone Avocadynofuran Azulene Baeckeol Bakerol Bancroftinone Barbatene Barbatene Bazzanene (β-> Benzaldehyde Benzaldehyde, dimethyl acetal Benzene Benzene Hydroxy citronellal Hydroxy citronellal



RT 10.12 10.02 34.24 34.16 11.65 11.30 14.99 35.51 20.88 21.07 19.64 19.40 19.28 17.49 26.62 17.23 21.11 08.05 32.05 15.40 23.83 13.50 17.59 32.12 33.91 11.53 21.54 59.05 33.18 41.72 36.72 28.20 26.68 29.48 28.86 28.05 30.08 32.01 33.48 34.91 34.45 39.79 63.50 64.33 63.30 41.80 42.93 37.24 26.82 26.16 33.20 26.19 23.11 16.87 13.87 19.60 30.14



19



AI 1063 1060 1635 1632 1103 1095 1181 1668 1315 1319 1287 1282 1279 1238 1447 1233 1320 1007 1579 1191 1382 1147 1241 1581 1626 1101 1330 2390 1607 1837 1699 1485 1449 1516 1500 1481 1530 1578 1615 1652 1640 1783 2557 2589 2549 1839 1871 1713 1452 1436 1608 1437 1366 1224 1155 1286 1532



Common Name Hydroxy citronellol Hydroxybenzaldehyde Hydroxybutanoic acid lactone Hydroxydiphenyl methane Incensole Incensole acetate Incensole oxide Indanol Indipone Indole Intermedeol Intermedeol Ionol Ionol Ionol Ionol Ionol acetate Ionol acetate Ionol acetate Ionone Ionone Ionone Ionone Ionone Ionone Ionone Ionone Ipsdienol Ipsenol Iridolactone Ishwarane Ishwarone Isoamyl 3-(2-furan)propionate Isoamyl acetoacetate Isoamyl angelate Isoamyl benzoate Isoamyl benzyl ether Isoamyl cinnamate Isoamyl dodecanoate Isoamyl geranate Isoamyl hexanoate Isoamyl isobutyrate Isoamyl nerolate Isoamyl nonanoate Isoamyl octanoate Isoamyl propionate Isoamyl tiglate Isobaeckeol Isobaeckeol methyl ether Isobazzanene Isobicyclogermacrenal Isoborneol Isoborneol Isobornyl 2-methyl butanoate Isobornyl acetate Isobornyl formate Isobornyl isobutanoate



RT 22.83 22.65 05.05 35.75 52.26 53.05 55.88 21.90 28.69 19.76 35.42 35.15 23.55 27.08 25.15 27.96 31.57 31.08 30.34 25.81 28.30 29.65 25.10 26.08 31.49 27.92 28.00 13.23 11.49 26.46 27.35 36.00 25.88 14.72 13.34 26.03 20.64 38.21 41.97 34.85 17.83 08.05 33.00 30.59 26.42 06.64 15.40 38.70 39.58 26.16 37.95 13.87 34.14 29.76 19.48 17.36 25.95



AI 1359 1355 0904 1674 2158 2184 2279 1338 1496 1290 1665 1658 1376 1458 1412 1479 1567 1555 1537 1428 1487 1520 1411 1434 1565 1478 1480 1140 1100 1443 1465 1680 1430 1175 1143 1433 1310 1740 1844 1650 1246 1007 1602 1543 1442 0960 1191 1753 1777 1436 1733 1155 1632 1523 1283 1235 1431



Adams: Essential Oil Components by GC/MS



20



Common Name RT Isobornyl isobutanoate 35.08 Isobornyl isobutanoate 33.04 Isobornyl isobutanoate 34.56 Isobornyl isobutanoate 35.75 Isobornyl isobutanoate 43.56 Isobornyl isovalerate 29.70 Isobornyl n-butanoate 27.72 Isobornyl propanoate 23.88 Isobutanol 02.00 Isobutyl acetate 02.81 Isobutyl acetoacetate 10.00 Isobutyl angelate 09.45 Isobutyl benzoate 21.39 Isobutyl cinnamate 33.80 Isobutyl formate 02.14 Isobutyl hexanoate 13.62 Isobutyl isobutyrate 05.18 Isobutyl phenylacetate 24.01 Isobutyl salicylate 25.59 Isobutyl tiglate 11.15 Isobutyl-(2E)-butenoate 07.62 Isocitral 14.82 Isocitral 14.06 Isocitral 13.21 Isocitronellene 05.46 Isocomene 24.05 Isocomene 24.94 Isocroweacin 30.98 Isodaucene 28.83 Isoelemicin 31.62 Isoelemicin 31.62 Isoeugenol 26.67 Isoeugenol 24.90 Isoeugenol acetate 33.46 Isoeugenol acetate 31.51 Isoeugenyl benzyl ether 51.24 Isoeugenyl benzyl ether 49.60 Isoeugenyl phenylacetate 56.42 Isoeugenyl phenylacetate 54.76 Isogeijerene C 17.83 Isohibaene 45.05 Isoledene 23.48 Isolimonene 07.22 Isolongifolan-7α-ol 33.59 Isolongifolanone 33.37 Isolongifolanone 33.88 Isomenthone 33.93 Isomenthone 19.92 Isomyristicin 33.52 Isopentyl 2-methyl butanoate 11.49 Isopentyl acetate 04.40 Isopentyl alcohol 02.53 Isopentyl butanoate 09.72 Isopentyl formate 03.06 Isopentyl isovalerate 11.60 Isopentyl salicylate 30.25 Isophorone 12.27



AI 1656 1603 1643 1674 1889 1521 1473 1383 0650 0761 1060 1045 1327 1623 0680 1149 0908 1386 1423 1088 0994 1177 1160 1140 0918 1387 1407 1553 1500 1568 1568 1448 1406 1614 1566 2125 2072 2297 2241 1246 1933 1374 0980 1618 1612 1625 1627 1293 1616 1100 0869 0731 1052 0788 1102 1535 1118



Common Name Isophorone Isophorone Isophyllocladene Isophytol Isopimara-9(11),15-diene Isopimarol Isopimpinellin Isoprenyl cinnamate Isoprenyl cinnamate Isoprenyl oxycoumarin Isopropyl butanoate Isopropyl hexadecanoate Isopropyl isobutyrate Isopropyl phenylacetate Isopropyl tetradecanoate Isopropyl tiglate Isopropyl-2-methoxypyrazine Isopropyl-2-methyl butyrate Isopropyl-4-methyl thiazole Isopropyl-5-methyl-(2E)-hexenal Isopropyl-5-methyl-(2Z)-hexenal Isopulegol Isopulegol Isopulegol Isopulegol Isopulegyl acetate Isopulegyl acetate Isopulegyl acetate Isopulegyl acetate Isoquinoline Isosafrole Isosafrole Isotorquatone Isotorquatone Isovalencenol Isovaleraldehyde Isovaleric acid Italicene Italicene Italicene epoxide Italicene epoxide Italicene ether Italicene ether Jasmolactone Jasmolactone Jasmolactone, extra C Jasmolactone, extra C Jasmone Jasmone Jasmatone Jasmatone Jasmone lactone Jasmone lactone Jasmonol Jasmonol Jasmonyl acetate Jasmonyl acetate



RT 13.23 16.48 46.18 45.52 44.11 56.77 54.63 49.40 46.34 50.95 03.81 48.09 03.08 18.77 41.42 06.93 11.14 04.59 08.24 11.66 12.00 13.43 13.86 13.37 14.38 19.10 19.45 19.05 20.73 17.97 23.45 21.82 40.42 41.96 40.15 02.04 03.66 24.84 24.69 30.74 29.40 30.30 29.45 28.45 28.31 32.02 31.51 24.19 24.26 23.67 24.12 28.14 27.56 21.43 21.18 24.55 26.84



AI 1140 1216 1966 1946 1905 2310 2237 2065 1970 2115 0836 2024 0790 1267 1828 0970 1090 0880 1012 1104 1112 1145 1155 1144 1167 1275 1283 1274 1312 1249 1373 1336 1800 1844 1793 0658 0827 1405 1401 1547 1514 1536 1515 1491 1487 1578 1566 1390 1392 1378 1388 1483 1470 1328 1322 1398 1452



Appendix I: Alphabetical List of Compounds



Common Name Jensenone Junenol Junicedranol Junicedranone Juvabione Juvabione Karahanaenone Kaur-15-ene Kaurene Kessane Khusilal Khusilol Khusimene Khusimol Khusimone Khusinol Khusinol acetate Kudtdiol Labd-13E-8,15-diol Labd-7,13-dien-15-ol Labd-7,13-dien-15-ol, acetate Laciniata furanone E Laciniata furanone F Laciniata furanone G Laciniata furanone H Lanceol Lanceol acetate Larixol Laurenan-2-one Laurenene Laurenene Lavandulol Lavandulol Lavandulol acetate Lavandulyl 2-methyl butanoate Lavandulyl acetate Lavandulyl acetate Lavandulyl isobutanoate Lavandulyl isovalerate Lavender lactone Leaf alcohol, ethyl acetal Ledol Leptospermone Leptospermone Libocedrol Liguloxide Ligustilide Ligustilide Lilial Limonen-10-ol Limonene Limonene aldehyde Limonene oxide (Me vs. IPP) Limonene oxide (Me vs. IPP) Linalool Linalool Linalool



RT 46.30 33.61 36.44 35.38 47.90 50.00 13.82 47.25 48.66 30.02 34.71 35.80 26.85 38.26 33.05 35.95 41.21 44.33 59.92 56.24 59.12 30.47 30.09 29.96 30.80 38.94 42.32 55.47 50.96 43.20 43.97 14.30 13.95 18.79 29.27 19.70 26.15 25.51 29.19 09.04 11.77 32.99 34.02 33.72 57.76 30.24 40.28 38.02 29.93 19.67 08.69 21.37 12.88 13.10 11.32 33.65 11.05



21



AI 1969 1618 1692 1664 2018 2085 1154 1997 2042 1529 1647 1675 1453 1741 1604 1679 1823 1912 2422 2291 2392 1540 1531 1528 1548 1760 1854 2265 2115 1879 1901 1165 1157 1268 1511 1288 1436 1421 1509 1034 1106 1602 1629 1621 2344 1534 1796 1734 1527 1288 1024 1326 1132 1137 1095 1619 1088



Common Name Linalool Linalool Linalool acetate Linalool acetate Linalool acetate Linalool butanoate Linalool formate Linalool isobutanoate Linalool isovalerate Linalool oxide (furanoid) Linalool oxide (pyranoid) Linalool oxide Linalool oxide Linalool oxide (furanoid) Linalool oxide (pyranoid) Linalool oxide acetate (pyranoid) Linalool propanoate Linalool Linoleic acid Lippifoli-1(6)-en-5-one Longiborneol (=Juniperol) Longiborneol acetate (=Juniperol acetate) Longicamphenylone Longicyclene Longifolene Longifolene Longifolol Longifolol Longifolol acetate Longipinanol Longipinanol Longipinene Longipinene Lyral Maaliol Macrocarpene Macrocarpene Macrocarpene Macrocarpene Macrocarpene Maltol Maltol propionate Maltyl isobutyrate Manool Manool Manool Manool Manool Manool oxide Manool oxide Manool oxide Manool oxide Maple furanone Massoia dodecalactone Massoia lactone Mayurone Mayurone



RT 12.82 11.43 18.16 18.99 17.15 25.53 16.42 23.43 27.43 10.29 14.52 08.01 07.52 10.89 14.64 19.64 21.73 34.97 51.47 30.89 32.85 36.16 31.35 23.37 24.92 24.14 37.25 37.80 41.09 31.58 31.35 22.41 24.64 35.41 31.53 29.92 29.31 27.59 29.88 28.81 11.77 26.99 28.58 49.11 49.20 58.18 56.41 54.63 46.89 47.64 54.02 57.55 15.02 36.20 27.60 36.85 32.70



AI 1131 1098 1254 1272 1231 1421 1214 1373 1466 1067 1170 1006 0991 1084 1173 1287 1334 1654 2132 1550 1599 1684 1562 1371 1407 1389 1713 1728 1819 1567 1562 1350 1400 1665 1566 1527 1512 1470 1526 1499 1106 1456 1494 2056 2059 2359 2297 2237 1987 2009 2216 2337 1182 1685 1471 1703 1595



Adams: Essential Oil Components by GC/MS



22



Common Name RT Mefranal 25.60 Melaleucol 36.98 Menth-1-en-7-al 21.56 Menth-1-en-7-al 19.00 Menth-1-en-9-ol 19.96 Menth-1-en-9-ol acetate 25.53 Menth-2-en-1-ol 12.29 Menth-2-en-1-ol 13.04 Menth-3-en-8-ol 13.45 Menth-6-en-2,8-diol 23.37 Mentha-1(7),8-dien-2-ol 17.00 Mentha-1(7),8-dien-2-ol 15.24 Mentha-1(7),8-diene 07.79 Mentha-1(7),8-diene 07.89 Mentha-1,4-dien-7-ol 21.30 Mentha-1,5-dien-8-ol 14.32 Mentha-2,4(8)-diene 10.94 Mentha-2,8-dien-1-ol 12.93 Mentha-2,8-dien-1-ol 12.33 Mentha-2,8-diene 07.31 Mentha-2,8-diene 07.18 Mentha-3,8-diene 10.30 Mentha-8-thiol-3-one 22.74 Mentha-8-thiol-3-one 23.36 Menthan-2-one 15.55 Menthan-2-one 15.75 Menthane 07.03 Menthatriene 11.86 Menthene 08.58 Menthene 07.32 Mentho thiophene 21.96 Menthofuran 14.05 Menthol 14.39 Menthol 21.44 Menthol 14.91 Menthol 14.13 Menthol 15.11 Mentholactone 23.05 Mentholactone 23.35 Menthone 13.55 Menthone 13.99 Menthyl acetate 19.93 Menthyl acetate 20.39 Menthyl acetate 18.92 Menthyl isovalerate 29.50 Menthyl lactate 28.05 Menthyl lactate 28.49 Menthyl lactate 27.44 Mercaptopropanoic acid 06.35 Mesitylene 07.61 Methoxy cinnamaldehyde 29.93 Methoxy cinnamic acid 36.77 Methoxy-3-(1-methylpropyl)pyrazine 14.42 Methyl 2-furoate 06.90 Methyl 2-octenoate 14.22 Methyl abietate 58.91 Methyl α-cyclogeranate 15.66



AI 1423 1706 1330 1273 1294 1421 1118 1136 1145 1371 1227 1187 1000 1003 1325 1166 1085 1133 1119 0983 0979 1068 1357 1371 1194 1199 0973 1108 1021 0984 1340 1159 1167 1328 1179 1161 1184 1364 1371 1148 1158 1294 1304 1271 1516 1481 1492 1467 0950 0994 1527 1700 1168 0969 1163 2385 1197



Common Name RT Methyl anthranilate 24.86 Methyl benzoate 11.07 Methyl benzyl butyrate 23.00 Methyl benzyl propanoate 19.31 Methyl biphenyl 28.35 Methyl butanoate 02.43 Methyl butanoate, 3-methyl-3-butenyl 12.03 Methyl butyl acetate 04.50 Methyl butyl benzoate 26.24 Methyl butyl isovalerate 11.65 Methyl butyl-2-methyl butyrate 11.50 Methyl chavicol 15.57 Methyl cinnamate 23.58 Methyl cinnamate 20.18 Methyl citronellate 18.33 Methyl communate 55.22 Methyl communate 54.47 Methyl cyclohexene 02.61 Methyl cyclohexylcarboxylate 09.84 Methyl daniellate 57.39 Methyl decanoate 21.23 Methyl decyl ketone (=2-dodecanone) 24.09 Methyl dehydroabietate 57.65 Methyl dihydrojasmonate 36.05 Methyl dihydrojasmonate 34.99 Methyl dodecanoate 29.82 Methyl eperuate 54.15 Methyl epi-jasmonate 35.91 Methyl eudesmate 37.40 Methyl eugenol 24.75 Methyl farnesoate 39.79 Methyl geranate 21.19 Methyl heptanoate 08.57 Methyl heptine carbonate 15.60 Methyl hexadecanoate 44.64 Methyl hexanoate 05.54 Methyl isoborneol 14.85 Methyl isoeugenol 28.47 Methyl isoeugenol 26.78 Methyl isopimarate 56.42 Methyl jasmonate 34.74 Methyl labdanolate 58.80 Methyl levopimarate 56.66 Methyl linoleate 50.33 Methyl myrtenate 19.92 Methyl neoabietate 60.48 Methyl nerolate 19.34 Methyl nidoresedate 58.96 Methyl nonanoate 16.83 Methyl octadecanoate 51.23 Methyl octanoate 12.50 Methyl octine carbonate 19.98 Methyl ο-anisate 21.72 Methyl p-tert-butylphenyl acetate 28.70 Methyl ρ-anisate 23.33 Methyl pent-2-enolide (impure) 06.21 Methyl pentanoate 03.55



AI 1405 1088 1363 1280 1488 0721 1112 0875 1438 1103 1100 1195 1376 1299 1257 2257 2231 0740 1055 2331 1323 1388 2341 1682 1654 1524 2220 1678 1718 1403 1783 1322 1021 1196 1921 0921 1178 1491 1451 2297 1648 2381 2306 2095 1293 2443 1280 2387 1223 2124 1123 1295 1334 1497 1371 0945 0821



Appendix I: Alphabetical List of Compounds



Common Name RT Methyl pentanoate 07.48 Methyl pentanoate 07.31 Methyl pentanoate 04.42 Methyl pentyl angelate 17.96 Methyl perillate 24.30 Methyl pimarate 54.65 Methyl propanoate 01.93 Methyl salicylate 15.35 Methyl sandaracopimarate 55.19 Methyl strictate 58.96 Methyl tetradecanoate 37.57 Methyl thujate 21.02 Methyl tiglate 04.28 Methyl undecanoate 25.66 Methyl vanillin 27.78 Methyl-(2E)-nonenoate 16.73 Methyl-(3E)-hexen-2-one 04.80 Methyl-(3E)-hexenoate 05.72 Methyl-(3Z)-hexen-2-one 04.40 Methyl-1-butanol 02.46 Methyl-1,4-cyclohexadiene 03.25 Methyl-2-butanol 02.10 Methyl-2-butenal 02.97 Methyl-2-cyclohexen-1-one 09.50 Methyl-2-pentanone 02.50 Methyl-3(2-furyl)acrolein 15.07 Methyl-3(2-furyl)acrolein 14.43 Methyl-7,13,15-abietatrienoate 62.05 Methyoxythiophenol 16.23 Mint sulfide 38.21 Modheph-2-ene 23.83 Modhephen-8β-ol 29.35 Musk ambrette 44.92 Musk ketone 46.80 Musk xylol 42.73 Mustakone 35.83 Muurol-5-en-4α-ol 31.24 Muurol-5-en-4β-ol 30.86 Muurol-5-en-4-one 36.31 Muurola-3,5-diene 26.64 Muurola-3,5-diene 26.78 Muurola-4(14),5-diene 27.35 Muurola-4(14),5-diene 28.53 Muurola-4,10(14)-dien-1β-ol 34.06 Muurolene 39.64 Muurolene 39.22 Muurolene 28.83 Muurolene 27.91 Muurolol (=Torreyol) 34.61 Muurolol 34.46 Myltayl-4(12)-ene 26.53 Myrac aldehyde 29.60 Myrcene 07.43 Myrcenol 12.32 Myrcenone 13.43 Myristicin 29.54 Myroxide 13.23



23



AI 0989 0983 0871 1249 1392 2237 0634 1190 2256 2387 1722 1318 0863 1424 1475 1221 0892 0927 0869 0724 0804 0671 0778 1046 0728 1183 1168 2501 1210 1740 1382 1513 1929 1984 1866 1676 1559 1550 1688 1448 1451 1465 1493 1630 1779 1767 1500 1478 1644 1640 1445 1519 0988 1119 1145 1517 1140



Common Name Myroxide Myrtanol Myrtanol Myrtanol acetate Myrtenal Myrtenol Myrtenyl acetate Naphthalene Naphthalene Naphthalene Naphthalene Naphthalene Naphthalene Necrodol Necrodol Necrodol acetate Necrodol acetate Neocallitropsene Neocnidilide Nepetalactone Nepetalactone Nepetalactone Neral Nerol Nerol oxide Nerolidol Nerolidol Nerolidyl acetate Nerolidyl acetate Nerolidyl isobutyrate Nerolidyl isobutyrate Nerone Nerone Neryl acetate Neryl acetone Neryl formate Neryl isobutanoate Neryl isovalerate Neryl propanoate Nezukol Nezukone Nicotine Niranin Nojigiku acetate Nonacosane Nonadecane Nonadienal Nonadienal Nonadienal Nonadienol Nonadienol Nonadienol Nonadienol acetate Nonadienol acetate Nonalactone Nonalactone Nonanal



RT 12.82 18.00 18.34 23.97 15.56 15.55 21.29 14.84 26.47 26.53 11.46 09.77 33.22 14.48 13.37 20.18 19.42 27.75 37.55 22.73 24.00 24.24 17.32 16.97 13.80 31.32 30.09 37.35 35.85 41.30 39.79 25.15 26.25 22.81 26.06 19.32 28.43 32.18 26.83 51.47 26.12 22.09 37.31 17.47 71.78 43.92 16.24 13.64 23.73 16.55 14.04 13.59 20.36 20.05 23.98 22.78 11.51



AI 1131 1250 1258 1385 1195 1194 1324 1178 1444 1445 1099 1053 1608 1169 1144 1299 1282 1474 1722 1357 1386 1391 1235 1227 1154 1561 1531 1716 1676 1825 1783 1412 1438 1359 1434 1280 1490 1582 1452 2132 1435 1342 1715 1238 2900 1900 1210 1150 1380 1217 1159 1149 1303 1296 1385 1358 1100



Adams: Essential Oil Components by GC/MS



24



Common Name RT Nonanal, dimethyl acetal 19.19 Nonane 04.93 Nonanoic acid 18.77 Nonanol 11.40 Nonanol 14.29 Nonanone 11.03 Nonanyl acetate 20.69 Nonen-1-al 13.94 Nonen-1-al 13.40 Nonen-1-ol 13.74 Nonenal 11.38 Nonenal 18.89 Nonenol 14.20 Nonenol 14.15 Nonenol 14.26 Nonenol acetate 20.49 Nonyne 21.16 Nootkatene 29.53 Nootkatin 45.95 Nootkatinol 50.10 Nootkatol 37.28 Nootkatol 36.72 Nootkatone 40.62 Nopinone 13.02 Nopol 19.23 Nopsan-4-ol 30.03 Nopyl acetate 25.65 Norbornen-2-ol 05.85 Norbornen-2-ol 06.05 Norbornen-2-ol acetate 11.22 Norbornen-2-ol acetate 11.05 Norbornene 02.50 Norbornene 03.30 Norbornene-2-methanol 10.30 Norbornene-2-methanol 09.95 Norbornene-2-methanol acetate 16.12 Norbornene-2-methanol acetate 15.90 Norborneol 07.26 Norborneol 06.93 Norborneol acetate 12.55 Norborneol acetate 12.59 Norpatchoulenol 31.00 Nuciferal 37.75 Nuciferal 37.25 Nuciferol 38.75 Nuciferol 37.63 Nuciferol acetate 41.47 Occidenol 35.85 Occidentalol 30.88 Occidentalol acetate 36.02 Occidol 41.68 Occidol acetate 46.51 Ocimene 09.42 Ocimene 08.96 Ocimene 12.70 Ocimene 13.20 Ocimenone 17.32



AI 1277 0900 1267 1097 1165 1087 1311 1157 1144 1152 1097 1270 1163 1162 1164 1306 1321 1517 1959 2088 1714 1699 1806 1135 1278 1529 1424 0932 0939 1092 1088 0728 0807 1068 1058 1207 1202 0982 0970 1124 1125 1553 1727 1713 1754 1724 1830 1676 1550 1681 1836 1975 1044 1032 1128 1140 1235



Common Name RT Ocimenone 16.94 Octacosane 69.55 Octadecane 40.40 Octadecanol 49.76 Octadecanol acetate 53.82 Octadecene 40.02 Octadienal 11.59 Octadienal 11.62 Octadienol 12.07 Octalactone 19.15 Octalactone 18.02 Octanal 07.72 Octane 14.72 Octane 03.17 Octanedioic acid, diethyl ester 32.25 Octanediol 21.92 Octanoic acid (=caprylic acid) 14.37 Octanol 07.60 Octanol 07.44 Octanol 10.11 Octanol acetate 16.30 Octanol acetate 12.35 Octanone 07.45 Octanone 07.19 Octanone 10.23 Octen-1-al 09.59 Octen-1-ol 10.03 Octen-1-ol 09.52 Octen-2-ol 07.28 Octen-2-ol 07.00 Octen-2-one 08.90 Octen-3-ol 07.04 Octen-3-ol butanoate 19.32 Octen-3-one 06.98 Octen-3-yl acetate 11.95 Octen-5-yne 06.59 Octene 03.45 Octene 03.32 Octene 03.20 Octene 03.06 Octenol 10.20 Octenol acetate 16.14 Octenol acetate 15.67 Octenol butanoate 24.03 Octenol propanoate 20.13 Octenyl cyclopentanone 29.97 Octyl formate 12.64 Oleic acid 51.75 Oplopanone 38.17 Oplopanonyl acetate 43.47 Oplopenone 33.17 Orcinol 23.23 Oroselone 52.08 Osthole 51.72 Oxazole 05.80 Oxofuranoeremophilane 42.10 Palustrol 31.56



AI 1226 2800 1800 2077 2209 1789 1102 1103 1113 1276 1250 0998 1175 0800 1584 1339 1167 0994 0988 1063 1211 1120 0988 0979 1066 1049 1060 1047 0982 0972 1030 0974 1280 0972 1110 0958 0815 0808 0801 0788 1065 1208 1197 1386 1298 1528 1127 2141 1739 1887 1607 1368 2152 2140 0930 1848 1567



Appendix I: Alphabetical List of Compounds



Common Name Panasinsene Papuanone Patchenol Patchenol Patchoulene Patchoulene Patchoulene Patchouli alcohol Pearlate (=3-octenol, propanoate) Pentacosane Pentadecane Pentadecanol Pentadecanone Pentadecen-2-one Pentanal Pentanal Pentandione Pentanoic acid Pentanoic acid Pentanol Pentanol Pentanol Pentanol Pentanol Pentanone Pentanone Penten-1-al Penten-3-ol Pentenoic acid Pentenoic acid Pentenol Pentyl benzoate Pentyl butanoate Pentyl cyclohexa-1,3-diene Pentyl furan Pentyl isobutanoate Pentyl propanoate Pentyl salicylate Perilla alcohol Perilla aldehyde Perilla ketone Perillene Peucenin, 7-methyl ether Phellandrene Phellandrene Phenethyl 2-furoate Phenethyl cinnamate Phenol Phenol Phenol Phenol acetate Phenol, 2-(1Z)-propenyl Phenyl ethane Phenyl ethyl 2-methylbutanoate Phenyl ethyl 3-methylbutanoate Phenyl ethyl acetate Phenyl ethyl acetate



RT 23.78 39.94 21.45 20.94 26.92 23.70 28.91 35.08 19.64 62.00 28.82 39.42 36.64 35.49 02.27 04.70 02.23 05.71 05.89 02.82 02.18 03.76 03.70 02.66 02.15 03.72 02.65 02.16 05.59 04.20 02.85 27.84 11.08 13.91 07.34 09.62 07.99 31.85 19.94 18.83 17.77 11.50 58.21 07.85 08.70 37.28 52.90 18.62 15.33 22.24 26.32 13.47 19.94 28.25 28.43 15.45 18.20



25



AI 1381 1787 1328 1316 1454 1379 1502 1656 1287 2500 1500 1773 1697 1667 0704 0886 0700 0927 0933 0762 0689 0833 0830 0745 0682 0831 0744 0684 0923 0858 0765 1476 1089 1156 0984 1049 1005 1574 1294 1269 1245 1102 2360 1002 1025 1714 2179 1264 1189 1346 1440 1146 1294 1486 1490 1192 1254



Common Name Phenyl ethyl alcohol Phenyl ethyl anthranilate Phenyl ethyl butanoate Phenyl ethyl formate Phenyl ethyl hexanoate Phenyl ethyl isobutanoate Phenyl ethyl octanoate Phenyl ethyl oxyacetaldehyde Phenyl ethyl phenyl acetate Phenyl ethyl propanoate Phenyl ethyl tiglate Phenyl heptan-3-one Phenyl hexan-3-one Phenyl pentan-3-one Phenyl propanal Phenyl propyl butanoate Phenyl propyl isobutanoate Phenyl-4-methyl-pentan-3-one Phenyl-tert-butanol Phloroacetophenone Phthalide Phyllocladanol Phyllocladene Phytol Phytol acetate Pimaradiene Pinane Pinane Pinanediol Pinchotene acetate Pinene Pinene Pinene hydrate Pinene hydrate Pinene oxide Pinene oxide Pinocampheol Pinocampheol Pinocamphone (=cis-3-pinanone) Pinocamphone Pinocamphone (=trans-3-pinanone) Pinocarveol Pinocarveol Pinocarvone Pinocarvyl acetate Pinocarvyl acetate Pinonic acid Piperitenone Piperitenone oxide Piperitol Piperitol Piperitol acetate Piperitol acetate Piperitone Piperitone epoxide (epoxide vs. IPP)



RT 11.75 51.28 26.27 14.60 34.46 24.31 42.03 21.28 44.38 22.47 32.25 29.83 25.58 21.80 11.58 28.12 26.24 23.77 13.79 35.47 34.15 53.83 47.86 45.37 54.07 45.59 07.27 06.91 21.01 27.50 05.85 07.04 13.18 12.33 11.45 13.83 14.32 14.78 14.57 17.85



AI 1106 2126 1439 1172 1640 1393 1846 1324 1913 1351 1584 1524 1423 1336 1102 1483 1438 1380 1153 1667 1632 2209 2016 1942 2218 1948 0982 0969 1318 1468 0932 0974 1139 1119 1099 1154 1166 1176 1172 1247



14.00 15.00 12.99 14.07 20.68 20.11 26.32 21.98 23.12 15.59 16.10 21.63 22.10 17.95



1158 1182 1135 1160 1311 1298 1440 1340 1366 1195 1207 1332 1343 1249



18.00



1250



Adams: Essential Oil Components by GC/MS



26



Common Name RT Piperitone epoxide 18.10 Piperonal 21.51 Piperonyl acetate 28.95 Pipitzol 41.82 Pipitzol 42.30 Platyphyllol 33.19 Pogostol 34.89 Polygodial 47.85 Pregeijerene 19.57 Pregeijerene B 19.05 Premnaspirodiene 29.05 Prenopsan-8-ol 31.91 Prenyl angelate 15.30 Prenyl benzoate 28.19 Prenyl cyclopentanone 16.86 Prenyl formate 03.62 Prenyl hexanoate 19.84 Prenyl isobutyrate 09.57 Prenyl limonene 26.44 Prenyl limonene 27.04 Presilphiperfol-7-ene 21.70 Presilphiperfolan-8-ol 32.30 Prezizaene 26.48 Procerin 44.98 Propanal, 3-methylthio04.97 Propanol, 3-methylthio06.90 Propyl butanoate 04.91 Propyl chromone 36.98 Propyl tiglate 08.99 Pseudo phytol 49.16 Pseudo phytol 47.91 Pseudo phytol 48.29 Pseudo phytol 46.93 Pseudoisoeugenyl 2-methylbutyrate 41.85 Pseudoisoeugenyl isobutyrate 38.24 Pseudowiddrene 28.75 Pulegol 16.95 Pulegol 16.35 Pulegone 17.27 Pygmaein 32.14 Pyran-2-one 27.89 Pyran-5-one 40.74 Pyran-5-one 40.49 Pyrazine 08.41 Pyrazine 13.89 Pyrazine 10.71 Pyrazine 05.29 Pyrazine 07.85 Pyrazine 04.86 Pyrazine 14.91 Pyrazine 06.85 Pyrazine 10.79 Pyrazine 05.38 Pyrazine 07.77



AI 1252 1329 1503 1840 1853 1607 1651 2016 1285 1274 1505 1575 1189 1485 1224 0825 1292 1048 1443 1457 1334 1585 1444 1931 0901 0969 0898 1706 1032 2058 2018 2030 1988 1841 1740 1498 1226 1213 1233 1581 1477 1809 1802 1017 1156 1079 0912 1002 0896 1179 0967 1081 0915 1000



Common Name Pyrazine Pyrazine Pyrazine Pyrazine Pyrazine Pyrazine Pyruvic acid Quinoline Raspberry ketone Raspberry ketone, methyl ether Resveratrol Retene Rimuene Rimuene Rosa-5,15-diene Rose oxide Rose oxide Rose oxide Rose oxide Rosefuran epoxide Rosifoliol Rotundene Sabina ketone Sabina ketone Sabinene Sabinene hydrate (IPP vs. OH) Sabinene hydrate (IPP vs. OH) Sabinene hydrate acetate (cis for Ac vs. IPP) Sabinene hydrate acetate (Ac vs. IPP) Sabinol (trans for OH vs. IPP) Sabinyl acetate (IPP vs. Acetyl) Safranal Safrole Salicylaldehyde Salicylate, 2-ethylhexylSalicylic acid, butyl ester Salicylic acid, hexyl ester Salvene Salvene Salvial-4(14)-en-1-one Sandalore Sandaracopimara-8(14),15-diene Sandaracopimarinal Sandaracopimarinol Santalene Santalene Santalene Santalenone Santalol Santalol Santalol Santalol Santalol acetate Santalol acetate Santalol acetate



RT 05.18 05.21 12.90 03.52 11.23 10.86 02.15 29.23 30.67 28.55 67.83 53.96 43.79 45.99 45.06 11.77 12.45 10.31 09.17 14.65 32.89 27.05 13.83 12.25 06.91 10.20 11.41



AI 0908 0909 1133 0819 1093 1083 0682 1510 1545 1493 2729 2214 1896 1960 1933 1106 1122 1068 1037 1173 1600 1457 1154 1117 0969 1065 1098



16.62



1219



18.12 13.10 19.73 15.64 19.56 09.23 40.65 27.54 35.75 04.20 04.01 32.66 28.72 46.26 53.06 55.58 25.31 27.05 26.51 31.92 38.15 37.31 36.84 35.74 42.79 39.59 41.05



1253 1137 1289 1196 1285 1039 1807 1469 1674 0858 0847 1594 1497 1968 2184 2269 1416 1457 1445 1576 1738 1715 1702 1674 1867 1777 1818



Appendix I: Alphabetical List of Compounds



Common Name Santalol acetate Santalone Santene Santolina alcohol Santolina triene Santolinyl acetate Santonine Sativene Sclarene Sclareol Sclareolide Sedanenolide Selin-11-en-4α-ol Selina-1,3,7(11)-trien-8-one Selina-1,3,7(11)-trien-8-one epoxide Selina-3,11-dien-6α-ol Selina-3,7(11)-diene Selinene Selinene Selinene Selinene Sempervirol Sesamol Seselin Sesquicineol-2-one Sesquicineole Sesquicineole Sesquicineole Sesquicineole Sesquilavandulol Sesquilavandulol Sesquilavandulyl acetate Sesquilavandulyl acetate Sesquiphellandrene Sesquisabinene Sesquisabinene hydrate Sesquisabinene hydrate (IPP vs. OH) Sesquithujene Sesquithujene Sesquithuriferol Seychellene Shisofuran Shyobunol Sibirene Silphinene Silphiperfol-4,7(14)-diene Silphiperfol-5-en-3-ol A Silphiperfol-5-en-3-ol B Silphiperfol-5-en-3-one A Silphiperfol-5-en-3-one B Silphiperfol-5-ene Silphiperfol-5-ene Silphiperfol-6-en-5-one Silphiperfol-6-ene Silphiperfolan-6α-ol Silphiperfolan-6β-ol



27



RT 40.60 14.82 04.66 09.06 05.12 14.54 53.65 24.21 46.45 54.21 49.40 37.45 35.14 34.15 38.46 34.54 30.66 29.67 28.74 28.37 28.49 55.98 20.69 47.27 36.81 29.44 39.16 27.62 27.54 34.10 33.16 38.19 37.92 29.70 27.05 30.56



AI 1805 1177 0884 1034 0906 1171 2203 1390 1974 2222 2065 1719 1658 1632 1746 1642 1545 1520 1498 1489 1492 2282 1311 1998 1701 1515 1766 1471 1469 1631 1607 1739 1732 1521 1457 1542



31.99 24.84 24.19 33.08 26.50 15.69 36.31 24.62 22.18 22.77 31.18 30.23 31.84 30.86 21.37 22.20 33.83 23.61 29.12 30.70



1577 1405 1390 1604 1444 1198 1688 1400 1345 1358 1557 1534 1574 1550 1326 1345 1624 1377 1507 1546



Common Name Silphiperfolan-6β-ol Silphiperfolan-7β-ol Sinensal Sinensal Skatole Spathulenol Spiroether Spiroether Spirolepechinene Squamulosone Stemone Stigmast-4-en-3-one Stilbene Stilbene Stilbene Styrene Styrene Sugiol Sylvestrene Sylvestrene Syringaldehyde Tagetone Tagetone Tagetone Tasmanone Taxodione Ternine Terpinen-4-ol Terpinen-4-ol acetate Terpinen-7-al Terpinen-7-al Terpinene Terpinene Terpineol Terpineol Terpineol Terpineol Terpineol Terpineol Terpineol Terpineol Terpineol Terpineol Terpinolene Terpinyl acetate Terpinyl acetate Terpinyl acetate Terpinyl acetate Terpinyl isobutanoate Tetracosane Tetradecanal Tetradecane Tetradecanol Tetradecatriene Tetradecene Tetrahydro jasmone Tetrahydro jasmone



RT 29.57 29.62 38.78 36.73 23.81 31.96 43.59 43.19 26.69 39.31 12.54 79.26 54.49 48.65 47.06 34.53 33.42 65.36 08.73 08.03 35.04 13.19 13.54 09.51 37.70 60.28 41.97 14.66 20.17 19.46 19.76 08.30 09.78 12.77 15.21 13.20 14.09 13.89 14.14 15.73 14.02 13.33 12.97 10.98 22.26 20.91 20.90 20.22 27.62 59.33 33.35 24.61 35.64 19.68 24.10 18.84 20.61



AI 1518 1519 1755 1699 1381 1577 1890 1879 1449 1770 1124 3237 2232 2042 1992 1642 1613 2629 1025 1007 1655 1139 1148 1046 1726 2435 1844 1174 1299 1283 1290 1014 1054 1130 1186 1140 1160 1156 1162 1199 1159 1143 1134 1086 1346 1316 1316 1300 1471 2400 1611 1400 1671 1288 1388 1269 1309



Adams: Essential Oil Components by GC/MS



28



Common Name Tetrahydrofuran Tetratriacontane Thiazole ethanol acetate Thiazole Thiazole Thiazole Thiazole Thiazole Thiazole Thiazole Thiazole Thio rose oxide Thio rose oxide Thiophene Thuj-3-en-10-al Thuja-2,4(10)-diene Thujanol Thujanol Thujanol Thujanol Thujanol acetate Thujanol acetate Thujanol acetate Thujanol acetate Thujaplicin Thujaplicin Thujaplicin Thujaplicinol Thujaplicinol Thujene Thujic acid Thujone Thujone Thujopsadiene Thujopsan-2α-ol Thujopsan-2β-ol Thujopsanone Thujopsanone Thujopsenal Thujopsene Thujopsenic acid Thymohydro quinone Thymol Thymol acetate Thymol, methyl ether Thymoquinone Tiglic acid Tiglic aldehyde Tolualdehyde Tolualdehyde Tolualdehyde Toluene Torquatone Torquatone Torulosol Totarene



RT



AI



05.29 82.80 24.18 02.54 08.32 06.38 08.89 07.62 03.42 05.75 17.23 19.05 19.95 09.89 14.99 06.44 14.26 12.94 13.60 13.50 19.98 18.75 19.04 19.38 25.06 27.79 28.12 29.20 30.32 05.62 23.75 11.56 12.00 27.38 32.34 32.44 34.95 34.48 37.06 25.86 42.65 30.99 19.71 22.38 17.19 17.93 05.20 02.58 10.15 10.09 10.66 28.09 40.94 42.75 58.21 44.68



0912 3400 1390 0732 1014 0951 1030 0994 0814 0928 1233 1274 1294 1057 1181 0953 1164 1134 1149 1147 1295 1267 1273 1281 1410 1475 1483 1509 1536 0924 1380 1101 1112 1465 1586 1588 1653 1641 1708 1429 1863 1553 1289 1349 1232 1248 0909 0737 1064 1062 1077 1482 1815 1866 2360 1922



Common Name Totarol Totarol , methyl ether Totarol Totarol , methyl ether Totarol acetate Totarolone Triacetin Triacontane Tricosane Tricyclene Tridecanal Tridecane Tridecanol Tridecanone Tridecen-1-al Tridecene Tridecenol Tridecenol acetate Trihydroxy benzaldehyde Trimenal Trimenal Trimethyl benzaldehyde Trimethyl benzaldehyde Trimethyl benzene Tripropionin Tritriacontane Turmerol Turmerone Turmerone Ugandensidial Umbellulone Undec-10-en-1-al Undec-9E-en-1-al Undec-9Z-en-1-al Undecadienal Undecalactone Undecalactone Undecanol Undecanal Undecanal Undecanal, dimethyl acetal Undecane Undecanol Undecanol Undecanol Undecanol Undecanol Undecanone Undecenal Undecenal Undecenol Undecenol Undecenol acetate Undecenol acetate Undecyne Untriacontane Valencene



RT 60.55 53.78 56.88 54.63 60.10 63.10 22.31 74.16 56.48 05.53 29.22 20.19 31.68 28.64 31.55 19.77 31.62 36.85 41.06 25.45 24.51 20.79 22.51 08.57 33.00 80.55 32.17 35.51 32.70 53.50 14.38 20.18 20.70 21.17 25.28 32.62 31.65 19.60 20.45 23.10 27.73 11.48 20.26 19.92 19.52 19.51 23.19 19.90 22.74 20.20 23.08 22.90 29.00 28.76 12.45 76.35 28.66



AI 2445 2208 2314 2237 2428 2542 1347 3000 2300 0921 1509 1300 1570 1495 1567 1290 1568 1703 1818 1419 1397 1313 1352 1021 1602 3300 1582 1668 1595 2198 1167 1299 1311 1322 1415 1593 1569 1286 1305 1365 1474 1100 1301 1293 1284 1284 1367 1293 1357 1300 1365 1361 1504 1498 1122 3100 1496



Appendix I: Alphabetical List of Compounds



Common Name Valencene Valencene Valeranone Valerianol Valeric acid Valerolactone Vanillin Vanillin Vanillin Vanillin acetate Vanillone, acetoVanillyl alcohol Veloutone Veltonal Veltonal Veratrole Verbanol Verbanol Verbanol Verbanol Verbanol acetate Verbanol acetate Verbanol acetate Verbanol acetate Verbenene Verbenol Verbenol Verbenone Verbenyl acetate Verbenyl acetate



RT 44.40 39.22 35.74 35.07 06.05 06.10 24.32 26.83 20.29 29.85 28.05 26.51 20.63 31.07 30.40 13.28 15.66 14.78 15.01 15.25 22.00 20.58 21.05 21.45 06.67 13.07 13.22 15.97 19.35 19.83



29



AI 1914 1767 1674 1656 0939 0941 1393 1452 1302 1525 1481 1445 1309 1555 1538 1141 1197 1176 1182 1187 1340 1308 1319 1328 961 1137 1140 1204 1280 1291



Common Name Vertocitral C Vertocitral C Vestitenone Vetiselinenol Vetispirene Vetispirene Vetivenene Vetivenene Vetivenic acid Vetivone Vetivone Viridene Viridiflorene (=Ledene) Viridiflorol Vulgarone B Warburganal Widdra-2,4(14)-diene Widdrol Xanthorrhizol Xanthostemone Ylangene Ylangene Yomogi alcohol Zerumbone Zierone Zingiberene Zizanal Zizanone Zonarene



RT 10.61 11.72 26.49 37.84 28.38 28.53 30.09 31.02 40.80 41.89 41.20 14.21 28.68 32.58 34.81 48.08 28.03 32.85 38.64 25.94 23.43 25.43 07.75 37.94 31.86 28.53 36.63 35.54 29.97



AI 1076 1105 1444 1730 1489 1493 1531 1554 1811 1842 1822 1163 1496 1592 1649 2023 1481 1599 1751 1431 1373 1419 0999 1732 1574 1493 1697 1668 1528



30



Adams: Essential Oil Components by GC/MS



Appendix II: Compounds Listed in Order of Elution on DB-5



31



Appendix II COMPOUNDS LISTED IN ORDER OF THEIR RETENTION TIME AND ARITHMETIC RETENTION INDEX ON DB-5



32



RT 1.63 1.80 1.88 1.93 1.99 2.00 2.00 2.02 2.04 2.10 2.14 2.15 2.15 2.16 2.18 2.23 2.23 2.25 2.27 2.33 2.34 2.43 2.45 2.46 2.50 2.50 2.53 2.54 2.58 2.61 2.65 2.66 2.81 2.81 2.82 2.83 2.85 2.85 2.88 2.88 2.90 2.97 3.03 3.03 3.04 3.05 3.06 3.06 3.06 3.08 3.10 3.14 3.15 3.17 3.17 3.19 3.20



Adams: Essential Oil Components by GC/MS



AI 529 606 600 634 647 650 650 654 658 671 680 682 682 684 689 700 700 702 704 711 711 721 723 724 728 728 731 732 737 740 744 745 760 761 762 763 765 765 769 769 771 778 785 785 786 787 788 788 788 790 792 796 797 800 800 801 801



Common Name Ethyl ether Ethyl acetate Hexane Methyl propanoate Dichloroethane Cyclobutanone Isobutanol Butanal, 2-methylIsovaleraldehyde Methyl-2-butanol Isobutyl formate Pentanone Pyruvic acid Penten-3-ol Pentanol Heptane Pentandione Ethyl furan Pentanal Ethoxy ethanol Ethyl propanoate Methyl butanoate Buten-1-ol Methyl-1-butanol Methyl-2-pentanone Norbornene Isopentyl alcohol Thiazole Tiglic aldehyde Methyl cyclohexene Penten-1-al Pentanol Cyclohexadiene Isobutyl acetate Pentanol Butanoic acid Buten-1-ol Pentenol Buten-2-ol acetate Hexen-3-ol Cyclohexadiene Methyl-2-butenal Butanediol Cyclohexene Cyclopentanol Butanethiol Dimethyl-3-pentanone Isopentyl formate Octene Isopropyl isobutyrate Hexenal Hexanol Hexenal Hexanedione Octane Hexanal Octene



RT 3.22 3.25 3.30 3.31 3.32 3.42 3.45 3.52 3.55 3.60 3.62 3.66 3.67 3.70 3.72 3.74 3.75 3.76 3.81 3.96 3.99 4.01 4.04 4.06 4.13 4.20 4.20 4.22 4.28 4.28 4.40 4.40 4.42 4.42 4.50 4.59 4.59 4.60 4.60 4.65 4.66 4.68 4.70 4.74 4.80 4.82 4.84 4.86 4.91 4.93 4.96 4.97 4.98 5.03 5.05 5.12 5.13



AI 802 804 807 807 808 814 815 819 821 824 825 827 828 830 831 832 832 833 836 844 846 847 849 850 854 858 858 859 863 863 869 869 871 871 875 880 880 881 881 884 884 885 886 889 892 893 894 896 898 900 901 901 901 903 904 906 907



Common Name Ethyl butanoate Methyl-1,4-cyclohexadiene Norbornene Butyl acetate Octene Thiazole Octene Pyrazine Methyl pentanoate Cyclohexene Prenyl formate Isovaleric acid Furfural Pentanol Pentanone Cyclohexene Butanoic acid Pentanol Isopropyl butanoate Hexenol Hexenal Salvene Ethyl isovalerate Hexenol Hexenol Pentenoic acid Salvene Hexenol Hexanol Methyl tiglate Isopentyl acetate Methyl-(3Z)-hexen-2-one Hexenol Methyl pentanoate Methyl butyl acetate Buten-1-ol acetate Isopropyl-2-methyl butyrate Allyl butanoate Butenoic acid, 3-methyl-2Ethyl pent-4-enoate Santene Heptanol Pentanal Heptanone Methyl-(3E)-hexen-2-one Heptenal Heptanol Pyrazine Propyl butanoate Nonane Ethyl pentanoate Propanal, 3-methylthioHeptanal Ethoxy ethyl acetate Hydroxybutanoic acid lactone Santolina triene Butyl propanoate



Appendix II: Compounds Listed in Order of Elution on DB-5



RT 5.14 5.18 5.18 5.19 5.20 5.21 5.25 5.29 5.29 5.29 5.32 5.32 5.35 5.38 5.46 5.46 5.46 5.46 5.48 5.53 5.53 5.54 5.59 5.61 5.62 5.63 5.66 5.71 5.71 5.72 5.75 5.78 5.80 5.80 5.81 5.82 5.83



AI 907 908 908 909 909 909 911 912 912 912 913 913 914 915 918 918 918 918 919 921 921 921 923 923 924 924 925 927 927 927 928 929 930 930 930 931 931



5.85 5.85 5.89 5.95 5.98 6.00 6.05 6.05 6.10 6.10 6.15 6.21 6.21 6.22 6.26 6.27 6.28 6.34 6.35



932 932 933 935 936 937 939 939 941 941 942 945 945 945 946 947 947 949 950



Common Name Hexadienal Isobutyl isobutyrate Pyrazine Acetylfuran Tiglic acid Pyrazine Amyl acetate Hexadienol Pyrazine Tetrahydrofuran Anisole Hexenyl formate Buten-1-ol , acetate Pyrazine Heptanone Heptanone (impure) Hexenyl formate Isocitronellene Acetonyl acetone Ethyl 2-methyl-4-pentenoate Tricyclene Methyl hexanoate Pentenoic acid Artemisia triene Thujene Cumene Heptanone Hepten-2-one Pentanoic acid Methyl-(3E)-hexenoate Thiazole Ethyl tiglate Citronellene Oxazole Ethyl 2-methyl pentanoate Allyl isovalerate Cyclopentene Norbornen-2-ol Pinene Pentanoic acid Cyclohexanol Heptanone Fruitaleur (=ethyl 2-methyl-3-pentenoate) Norbornen-2-ol Valeric acid Acetoxyhexane Valerolactone Citronellene Cyclohexanone Methyl pent-2-enolide (impure) Fenchene Camphene Heptenal Heptenol Ethyl 3-methyl pentanoate Glycerol



33



RT 6.35 6.38 6.43 6.44 6.49 6.56 6.58 6.58 6.59 6.63 6.63 6.64 6.67 6.84 6.85 6.90 6.90 6.91 6.91 6.93 6.93 6.96 6.98 7.00 7.01 7.02 7.03 7.04 7.04 7.18 7.19 7.22 7.25 7.26 7.27 7.28 7.30 7.31 7.31 7.32 7.34 7.39 7.42 7.43 7.44 7.45 7.45 7.47 7.48 7.48 7.52 7.58 7.60 7.61 7.62 7.62 7.71



AI 950 951 952 953 954 957 958 958 958 959 959 960 961 967 967 969 969 969 969 970 970 971 972 972 973 973 973 974 974 979 979 980 981 982 982 982 983 983 983 984 984 986 987 988 988 988 988 989 989 989 991 993 994 994 994 994 997



Common Name Mercaptopropanoic acid Thiazole Benzaldehyde Thuja-2,4(10)-diene Cyclohexyl formate Furfural Heptan-2-ol Hepten-1-ol Octen-5-yne Heptanol Hepten-1-ol Isoamyl propionate Verbenene Hexanoic acid (=caproic acid) Pyrazine Methyl 2-furoate Propanol, 3-methylthioPinane Sabinene Isopropyl tiglate Norborneol Artemiseole Octen-3-one Octen-2-ol Hexanal, dimethyl acetal Dimethyl-4-heptanone Menthane Octen-3-ol Pinene Mentha-2,8-diene Octanone Isolimonene Hepten-2-one Norborneol Pinane Octen-2-ol Hexenoic acid Mentha-2,8-diene Methyl pentanoate Menthene Pentyl furan Decene Furfuryl acetate Myrcene Octanol Cineole Octanone Hepten-2-ol Heptanol Methyl pentanoate Linalool oxide Butyl butanoate Octanol Mesitylene Isobutyl-(2E)-butenoate Thiazole Ethyl hexanoate



34



RT 7.72 7.74 7.75 7.77 7.77 7.79 7.84 7.84 7.85 7.85 7.89 7.91 7.93 7.96 7.99 7.99 7.99 8.01 8.03 8.05 8.05 8.10 8.17 8.18 8.22 8.24 8.27 8.30 8.32 8.34 8.41 8.41 8.43 8.51 8.53 8.57 8.57 8.57 8.58 8.59 8.69 8.70 8.73 8.76 8.77 8.80 8.83 8.89 8.90 8.95 8.96 8.99 9.03 9.04 9.06 9.14 9.17



Adams: Essential Oil Components by GC/MS



AI 998 998 999 1000 1000 1000 1001 1001 1002 1002 1003 1003 1004 1005 1005 1005 1005 1006 1007 1007 1007 1008 1010 1011 1012 1012 1013 1014 1014 1015 1017 1017 1017 1019 1020 1021 1021 1021 1021 1022 1024 1025 1025 1026 1026 1027 1028 1030 1030 1031 1032 1032 1033 1034 1034 1036 1037



Common Name Octanal Furfuryl methyl sulfide Yomogi alcohol Decane Pyrazine Mentha-1(7),8-diene Carene Hexenyl acetate Phellandrene Pyrazine Mentha-1(7),8-diene Ethyl-(3E)-hexenoate Hexenyl acetate Cresol methyl ether Heptadienal Hexenoic acid Pentyl propanoate Linalool oxide Sylvestrene Hexyl acetate Isoamyl isobutyrate Carene Hexenyl acetate Dichlorobenzene Cineole Isopropyl-4-methyl thiazole Heptadienol Terpinene Thiazole Anisole Ethyl 2-methyl-2-pentenoate Pyrazine Cyclopentanedione Ethyl 2-methyl-2-pentenoate Cymene Allyl tiglate Methyl heptanoate Trimethyl benzene Menthene Cymene Limonene Phellandrene Sylvestrene Cineole Benzyl alcohol Hexanoic acid Acetyl pyridine Thiazole Octen-2-one Furan Ocimene Propyl tiglate Hexanoic acid Lavender lactone Santolina alcohol Benzene acetaldehyde Rose oxide



RT 9.19 9.20 9.23 9.33 9.42 9.45 9.50 9.51 9.51 9.52 9.57 9.59 9.62 9.64 9.65 9.67 9.72 9.77 9.78 9.79 9.84 9.88 9.89 9.92 9.95 9.99 10.00 10.02 10.03 10.09 10.11 10.11 10.12 10.15 10.20 10.20 10.22 10.23 10.29 10.30 10.30 10.31 10.35 10.43 10.43 10.45 10.52 10.61 10.66 10.70 10.71 10.72 10.76 10.76 10.78 10.79 10.80



AI 1038 1038 1039 1042 1044 1045 1046 1046 1046 1047 1048 1049 1049 1050 1050 1051 1052 1053 1054 1054 1055 1056 1057 1057 1058 1059 1060 1060 1060 1062 1063 1063 1063 1064 1065 1065 1066 1066 1067 1068 1068 1068 1069 1071 1071 1072 1074 1076 1077 1078 1079 1079 1080 1080 1081 1081 1081



Common Name Heptyl acetate Ethyl hex-(2E)-enoate Salicylaldehyde Hexalactone Ocimene Isobutyl angelate Methyl-2-cyclohexen-1-one Arbusculone Tagetone Octen-1-ol Prenyl isobutyrate Octen-1-al Pentyl isobutanoate Ethyl levulinate Cresol Bergamal Isopentyl butanoate Naphthalene Terpinene Acetylpyrrole Methyl cyclohexylcarboxylate Artemisia ketone Thiophene Benzene methanol Norbornene-2-methanol Acetophenone Isobutyl acetoacetate Hexenyl oxy-acetaldehyde Octen-1-ol Tolualdehyde Hexadienol acetate Octanol Hexenyl oxy-acetaldehyde Tolualdehyde Octenol Sabinene hydrate (IPP vs. OH) Arbusculone Octanone Linalool oxide (furanoid) Mentha-3,8-diene Norbornene-2-methanol Rose oxide Dihydro myrcenol Benzyl formate Cresol Cresol Heptanal, dimethyl acetal Vertocitral C Tolualdehyde Camphenilone Pyrazine Allyl hexanoate Artemisia alcohol Benzene Acetyl-2,5-dimethyl furan Pyrazine Hexenal , diethyl acetal



Appendix II: Compounds Listed in Order of Elution on DB-5



RT 10.82 10.86 10.88 10.88 10.89 10.94 10.94 10.94 10.97 10.98 11.00 11.01 11.03 11.05 11.05 11.07 11.08 11.09 11.11 11.14 11.14 11.14 11.15 11.19 11.20 11.22 11.23 11.30 11.32 11.32 11.38 11.40 11.40 11.41 11.42 11.42 11.43 11.44 11.45 11.46 11.48 11.49 11.49 11.50 11.50 11.51 11.53 11.56 11.56 11.58 11.59 11.60 11.60 11.62 11.65 11.65 11.66



AI 1082 1083 1083 1083 1084 1085 1085 1085 1086 1086 1087 1087 1087 1088 1088 1088 1089 1089 1090 1090 1090 1090 1088 1092 1092 1092 1093 1095 1095 1095 1097 1097 1097 1098 1098 1098 1098 1099 1099 1099 1100 1100 1100 1100 1102 1100 1101 1101 1101 1102 1102 1102 1102 1103 1103 1103 1104



Common Name Cymenene Pyrazine Fenchone Furfuryl propionate Linalool oxide (furanoid) Butyl angelate Cyclohexanedione Mentha-2,4(8)-diene Acetyl thiophene Terpinolene Guaiacol Hexenal Azulene Geranyl formate Pinocarvyl acetate Carquejol acetate Octenol propanoate



39



RT 20.14 20.17 20.18 20.18 20.18 20.19 20.20 20.22 20.26 20.29 20.29 20.36 20.36 20.39 20.40 20.42 20.45 20.48 20.48 20.49 20.58 20.59 20.61 20.63 20.63 20.64 20.64 20.68 20.69 20.69 20.70 20.73 20.74 20.75 20.79 20.83 20.87 20.88 20.90 20.91 20.93 20.94 20.96 21.00 21.01 21.02 21.04 21.04 21.05 21.07 21.07 21.11 21.16 21.17 21.18 21.19 21.23



AI 1298 1299 1299 1299 1299 1300 1300 1300 1301 1302 1302 1303 1303 1304 1304 1305 1305 1306 1306 1306 1308 1309 1309 1309 1309 1310 1310 1311 1311 1311 1311 1312 1312 1312 1313 1314 1315 1315 1316 1316 1316 1316 1317 1318 1318 1318 1319 1319 1319 1319 1319 1320 1321 1322 1322 1322 1323



Common Name Carvacrol Terpinen-4-ol acetate Methyl cinnamate Necrodol acetate Undec-10-en-1-al Tridecane Undecenal Terpinyl acetate Undecanol Elsholtzia ketone Vanillin Cinnamyl alcohol Nonadienol acetate Menthyl acetate Butanoic acid, 2-methyl-4-methylhexyl ester Cresol isobutyrate Undecanal Dihydro carveol acetate Dihydro carveol acetate Nonenol acetate Verbanol acetate Guaiacol Tetrahydro jasmone Carvotanacetone Veloutone Adamantanone Isoamyl benzyl ether Pinocarvyl acetate Nonanyl acetate Sesamol Undec-9E-en-1-al Isopulegyl acetate Cyclohexanol acetate Citronellic acid Trimethyl benzaldehyde Cryptone Decadienal Hexenyl tiglate Terpinyl acetate Terpinyl acetate Citral Patchenol Cycloisolongifolene Cinnamaldehyde Pinanediol Methyl thujate Dihydro citronellol acetate Dimethyl phenethyl acetate Verbanol acetate Decadienol Hexenyl tiglate Hexyl 2-methyl-3-pentenoate Nonyne Undec-9Z-en-1-al Jasmonol Methyl geranate Methyl decanoate



40



RT 21.28 21.29 21.30 21.36 21.37 21.37 21.39 21.39 21.43 21.44 21.45 21.45 21.51 21.52 21.54 21.56 21.63 21.68 21.70 21.72 21.72 21.73 21.76 21.77 21.80 21.82 21.85 21.90 21.90 21.92 21.92 21.95 21.95 21.96 21.97 21.98 22.00 22.09 22.10 22.13 22.18 22.20 22.24 22.26 22.30 22.30 22.31 22.33 22.38 22.41 22.41 22.47 22.48 22.51 22.57 22.64 22.65



Adams: Essential Oil Components by GC/MS



AI 1324 1324 1325 1326 1326 1326 1327 1327 1328 1328 1328 1328 1329 1330 1330 1330 1332 1333 1334 1334 1334 1334 1335 1335 1336 1336 1337 1338 1338 1339 1339 1339 1339 1340 1340 1340 1340 1342 1343 1343 1345 1345 1346 1346 1347 1347 1347 1345 1349 1350 1350 1351 1351 1352 1353 1355 1355



Common Name Phenyl ethyl oxyacetaldehyde Myrtenyl acetate Mentha-1,4-dien-7-ol Dihydro carveol acetate Limonene aldehyde Silphiperfol-5-ene Hasmigone Isobutyl benzoate Jasmonol Menthol Patchenol Verbanol acetate Piperonal Anisyl formate Hexyl tiglate Menth-1-en-7-al Piperitol acetate Hasmigone Presilphiperfol-7-ene Anthranilate Methyl ο-anisate Linalool propanoate Benzenemethanol Elemene Phenyl pentan-3-one Isosafrole Evodone Citral Indanol Benzenemethanol(3-hydroxy-> Octanediol Butanone Carvyl acetate Mentho thiophene Dihydroisojasmone Piperitenone Verbanol acetate Nicotine Piperitol acetate Benzyl butanoate Silphinene Silphiperfol-5-ene Phenol Terpinyl acetate Acetophenone Catalponone Epoxy-pseudoisoeugenyl 2-methylbutyrate Rimuene Cedrane-diol Nonadecane Columellarin Laurenene Evodione Isopimara-9(11),15-diene Kudtdiol Farnesyl acetone Phenyl ethyl phenyl acetate Valencene Methyl hexadecanoate Totarene Carissone Musk ambrette Dictamine Beyerene Procerin Cuparenic acid Isohibaene Rosa-5,15-diene Cyclohexadecanolide Cembrene Acetoxyeudesman-4α-ol Callitrisin Drimenin Phytol Isophytol Cembrene A Pimaradiene Columellarin Geranyl benzoate Hexadecanoic acid Nootkatin Geranyl linalool Chenopodiol-6-acetate Rimuene Cembrene A



50



RT 46.18 46.25 46.26 46.30 46.34 46.42 46.45 46.45 46.51 46.56 46.69 46.80 46.84 46.89 46.90 46.92 46.93 46.94 47.06 47.09 47.25 47.27 47.29 47.33 47.35 47.45 47.64 47.75 47.82 47.85 47.86 47.90 47.91 48.03 48.08 48.08 48.09 48.16 48.29 48.39 48.44 48.65 48.66 48.75 49.08 49.10 49.11 49.16 49.20 49.40 49.40 49.60 49.76 50.00 50.08 50.10 50.22



Adams: Essential Oil Components by GC/MS



AI 1966 1968 1968 1969 1970 1973 1974 1974 1975 1977 1981 1984 1985 1987 1987 1987 1988 1988 1992 1992 1997 1998 1998 2000 2000 2003 2009 2013 2015 2016 2016 2018 2018 2022 2023 2023 2024 2026 2030 2033 2035 2042 2042 2045 2055 2056 2056 2058 2059 2065 2065 2072 2077 2085 2087 2088 2092



Common Name Isophyllocladene Callitrisin Sandaracopimara-8(14),15-diene Jensenone Isoprenyl cinnamate Dolabradiene Ferula lactone I Sclarene Occidol acetate Bifloratriene Coumarin Musk ketone Amorpha-4,7(11)-dien-8-one Manool oxide Geranyl linalool Eicosene Pseudo phytol Catalponol Stilbene Ethyl hexadecanoate Kaur-15-ene Seselin Geranyl linalool Eicosane Dolabradiene Hexadecyl acetate Manool oxide Coumarin Ethylene brassylate Polygodial Phyllocladene Juvibione Pseudo phytol Abieta-8,12-diene Catalponol Warburganal Isopropyl hexadecanoate Geranyl linalool Pseudo phytol Bergaptene Falcarinol Stilbene Kaurene Canellal Abietatriene Bergaptene Manool Pseudo phytol Manool Isoprenyl cinnamate Sclareolide Isoeugenyl benzyl ether Octadecanol Juvibione Abietadiene Nootkatinol Benzyl cinnamate



RT 50.33 50.47 50.95 50.96 51.23 51.24 51.28 51.47 51.47 51.72 51.75 51.98 52.08 52.12 52.26 52.76 52.90 52.93 53.05 53.06 53.22 53.43 53.50 53.53 53.54 53.65 53.78 53.82 53.83 53.96 54.02 54.04 54.07 54.15 54.21 54.47 54.49 54.63 54.63 54.63 54.65 54.75 54.76 55.19 55.22 55.47 55.58 55.74 55.88 55.98 56.24 56.41 56.42 56.42 56.44 56.48 56.66



AI 2095 2100 2115 2115 2124 2125 2126 2132 2132 2140 2141 2149 2152 2153 2158 2174 2179 2180 2184 2184 2189 2196 2198 2199 2200 2203 2208 2209 2209 2214 2216 2217 2218 2220 2222 2231 2232 2237 2237 2237 2237 2241 2241 2256 2257 2265 2269 2274 2279 2282 2291 2297 2297 2297 2298 2300 2306



Common Name Methyl linoleate Heneicosane Isoprenyl oxycoumarin Laurenan-2-one Methyl octadecanoate Isoeugenyl benzyl ether Phenyl ethyl anthranilate Linoleic acid Nezukol Osthole Oleic acid Abienol Oroselone Abieta-(8(14),13(15)-diene Incensole Grandiflorene Phenethyl cinnamate Citronellyl anthranilate Incensole acetate Sandaracopimarinal Docosene Ethyl octadecanoate Ugandensidial Catalpalactone Docosane Santonine Totarol , methyl ether Octadecanol acetate Phyllocladanol Retene Manool oxide Geranyl anthranilate Phytol acetate Methyl eperuate Sclareol Methyl communate Stilbene Isopimpinellin Manool Totarol , methyl ether Methyl pimarate Decyl anthranilate Isoeugenyl phenylacetate Methyl sandaracopimarate Methyl communate Larixol Sandaracopimarinol Abietal, dehydro Incensole oxide Sempervirol Labd-7,13-dien-15-ol Manool Isoeugenyl phenylacetate Methyl isopimarate Abietal Tricosane Methyl levopimarate



Appendix II: Compounds Listed in Order of Elution on DB-5



RT 56.77 56.85 56.87 56.88 56.92 57.17 57.39 57.39 57.55 57.65 57.72 57.76 58.18 58.21 58.21 58.28 58.35 58.42 58.50 58.80 58.91 58.96 58.96 59.05 59.12 59.33 59.37 59.63 59.92 60.10 60.28 60.48 60.55 60.84 61.15 62.00 62.05 63.10 63.30 63.50 64.33 64.61 65.36 67.12 67.83 69.55 71.78 74.16 76.35 78.48 79.26 80.55 82.80



AI 2310 2312 2313 2314 2315 2324 2331 2331 2337 2341 2343 2344 2359 2360 2360 2363 2365 2368 2370 2381 2385 2387 2387 2390 2392 2400 2401 2411 2422 2428 2435 2443 2445 2456 2468 2500 2501 2542 2549 2557 2589 2600 2629 2700 2729 2800 2900 3000 3100 3200 3237 3300 3400



Common Name Isopimarol Abieta-7,13-diene-3-one Abietal Totarol Ferruginol Abietadien-18-ol Ferruginol Methyl daniellate Manool oxide Methyl dehydroabietate Abietol Libocedrol Manool Peucenin, 7-methyl ether Torulosol Ferruginol acetate Communic acid Abietol, dehydro Ferruginol Methyl labdanolate Methyl abietate Methyl nidoresedate Methyl strictate Heyderiol Labd-7,13-dien-15-ol, acetate Tetracosane Abietol Ferruginol acetate Labd-13E-8,15-diol Totarol acetate Taxodione Methyl neoabietate Totarol Ferruginol Abietol Pentacosane Methyl-7,13,15-abietatrienoate Totarolone Hinokione Hinokienone Hinokiol Hexacosane Sugiol Heptacosane Resveratrol Octacosane Nonacosane Triacontane Untriacontane Dotriacontane Stigmast-4-en-3-one Tritriacontane Tetratriacontane



51



52



Adams: Essential Oil Components by GC/MS



Appendix III: Mass Spectra



53



Appendix III MASS SPECTRA AND STRUCTURES OF COMPOUNDS LISTED IN ORDER OF THEIR RETENTION TIME/ ARITHMETIC INDEX ON DB-5



Adams: Essential Oil Components by GC/MS



54



RT: 1.63 AI: 529 KI: 540 Ethyl ether CAS#: 60-29-7 MF: C4 H10 O FW: 74 CN: ethyl ether Synonyms: diethyl ether Source: VWR Scientific 100



45



MSD LIB#: 1561



59



80



O



74



60 40 20 60



80



100



120



140



RT: 1.80 AI: 606 KI: 609 Ethyl acetate CAS#: 141-78-6 MF: C4 H8 O2 FW: 88 MSD LIB#: 1865 CN: acetic acid, ethyl ester Synonyms: acetic ether; acetidin; ethyl ethanoate Source: VWR Scientific; 57.39% Cananga odorata, Sepu. 6:11(1988); 6.40% Bouea macrophylla; 3.79% Brassica juncea (seed) O



O



RT: 1.88 AI: 623 KI: 632 Hexane CAS#: 110-54-3 MF: C6 H14 FW: 86 MSD LIB#: 1430 CN: n-hexane Synonyms: none Source: Sigma Chem.; 2.60% Thymus vulgaris, Bioflavour 87:327(1988); 0.12% Artemisia annua; 0.10% Apium graveolens 100



41



57



80 60 40 20



86



71 40



60



80



100



Appendix III: Mass Spectra



55



RT: 1.93 AI: 634 KI: 645 Methyl propanoate CAS#: 554-12-1 MF: C4 H8 O2 FW: 88 CN: propanoic acid, methyl ester Synonyms: methyl propionate Source: Aldrich Chem.



MSD LIB#: 1110



57



100



O



80 O



60 40



88



20



45 60



80



100



120



140



RT: 1.99 AI: 647 KI: 658 Dichloroethane CAS#: 107-06-2 MF: C2 H4 Cl2 FW: 98 MSD LIB#: 591 CN: ethane, 1,2-dichloroSynonyms: none Source: Matheson-Coleman Co. 62



100



CH2Cl



80



CH2Cl



60 40



49



20



98 60



80



100



RT: 2.00 AI: 650 KI: 660 Cyclobutanone CAS#: 1191-95-3 MF: C4 H6 O FW: 70 CN: cyclobutanone Synonyms: none Source: Aldrich Chem. ex JJ Brophy 100



120



140



MSD LIB#: 2014



42 O



80 60 40



70



20 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



56



RT: 2.00 AI: 650 KI: 660 Isobutanol CAS#: 78-83-1 MF: C4 H10 O FW: 74 CN: 1-propanol, 2-methylSynonyms: isobutyl alcohol Source: Aldrich Chem. 100



MSD LIB#: 1609



41 OH



80 60 40 59



20



74



60



80



100



120



140



RT: 2.02 AI: 654 KI: 664 Butanal CAS#: 96-17-3 MF: C5 H10 O FW: 86 MSD LIB#: 1703 CN: butanal, 2-methylSynonyms: none Source: Aldrich Chem.



O



RT: 2.04 AI: 658 KI: 668 Isovaleraldehyde CAS#: 590-86-3 MF: C5 H10 O FW: 86 MSD LIB#: 1631 CN: butanal, 3-methylSynonyms: isovaleral, isopentanal, butanal Source: Aldrich Chem. 100



43 O



80 60 40



71



57



20



86 60



80



100



120



140



Appendix III: Mass Spectra



57



RT: 2.10 AI: 671 KI: 679 Methyl-2-butanol CAS#: 598-75-4 MF: C5 H12 O FW: 88 MSD LIB#: 1639 CN: 2-butanol, 3-methylSynonyms: sec-Isoamyl alcohol Source: Aldrich Chem. OH



RT: 2.14 AI: 680 KI: 686 Isobutyl formate CAS#: 542-55-2 MF: C5 H10 O2 FW: 102 MSD LIB#: 1613 CN: formic acid, 2-methylpropyl ester Synonyms: isobutyl methanoate Source: Aldrich Chem.; 0.06% Ocimum basillicum, FFJ 6:225(1991) 56



100



O



80



O



43



60 40 20 40



60



80



100



120



RT: 2.15 AI: 682 KI: 687 Pentanone CAS#: 107-87-9 MF: C5 H10 O FW: 86 MSD LIB#: 1571 CN: 2-pentanone Synonyms: none Source: Aldrich Chem.; 9.10% Psidium guajava, FFJ 6:143(1991); 1.85% Zizyphus jujuba; 0.30% Hedyotis diffusa 100



43 O



80 60 40 20



58 60



86



71 80



100



120



140



Adams: Essential Oil Components by GC/MS



58



RT: 2.15 AI: 682 KI: 687 Pyruvic acid CAS#: 127-17-3 MF: C3 H4 O3 FW: 88 CN: propanoic acid, 2-oxoSynonyms: pyroacemic acid; acetyl formic acid Source: Bedoukian Res.



MSD LIB#: 2059



O O



OH



RT: 2.16 AI: 684 KI: 689 Penten-3-ol CAS#: 616-25-1 MF: C5 H10 O FW: 86 MSD LIB#: 1710 CN: 1-penten-3-ol Synonyms: ethyl vinyl carbinol Source: Aldrich Chem.; 0.36% Comptonia peregrina, FFJ 3:65(1988); 0.13% Chloranthus spicatus; 0.05% Tilia cordata OH



RT: 2.18 AI: 689 KI: 692 Pentanol CAS#: 6032-29-7 MF: C5 H12 O FW: 88 MSD LIB#: 1813 CN: 2-pentanol Synonyms: sec-pentanol, pentyl alcohol Source: alcohols mix (2-OHs) ex K-H Kubeczka; 7.00% Psidium guajava, FFJ 6:143(1991); 0.85% Michelia figo; 0.10% Narcissus tazetta OH



Appendix III: Mass Spectra



59



RT: 2.23 AI: 700 KI: 700 Heptane CAS#: 142-82-5 MF: C7 H16 FW: 100 MSD LIB#: 101 CN: heptane Synonyms: skellysolve C Source: alkanes mix, Alltech Assoc.; 3.21% Cymbidium sinense, p. 110, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 1.79% Elettaria cardamomum (seed); 0.50% Carlina acaulis (root) 100



43



80 60



71



57



40



100



20 60



80



100



RT: 2.23 AI: 700 KI: 700 Pentandione CAS#: 600-14-6 MF: C5 H8 O2 FW: 100 CN: 2,3-pentanedione Synonyms: acetylpropionyl Source: Aldrich Chem. 100



120



140



MSD LIB#: 1247



43



80 O



60 40



O



57



20



100 60



80



100



120



140



RT: 2.25 AI: 702 KI: 703 Ethyl furan CAS#: 3208-16-0 MF: C6 H8 O FW: 96 MSD LIB#: 2071 CN: furan, 2-ethylSynonyms: none Source: Bedoukian Res.; 0.05% Mentha piperita, Chimika Chronika 9:13(1980); 0.02% Ocimum basilicum; 0.01% Citrus medica (leaf) 81



100



O



80 60 40



96 53



20 41



67 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



60



RT: 2.27 AI: 704 KI: 706 Pentanal CAS#: 110-62-3 MF: C5 H10 O FW: 86 MSD LIB#: 1245 CN: pentanal Synonyms: valeraldehyde Source: Aldrich Chem.; 2.25% Tilia cordata (blossom flower), FFJ 1:57(1986); 2.00% Mentha arvensis; 1.02% Gardenia jasminoides O



RT: 2.33 AI: 711 KI: 715 Ethoxy ethanol CAS#: 110-80-5 MF: C4 H10 O2 FW: 90 MSD LIB#: 1748 CN: ethanol, 2-ethoxySynonyms: cellusolve, ethyl glycol Source: Baker Chem. 100



45



80



O



59



OH



60 40 72



20 60



80



100



120



140



RT: 2.34 AI: 711 KI: 716 Ethyl propanoate CAS#: 105-37-3 MF: C5 H10 O2 FW: 102 MSD LIB#: 75 CN: propanoic acid, ethyl ester Synonyms: ethyl propionate Source: Aldrich Chem.; 0.37% Artabotrys hexapetalus, p. 90, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993) 57



100 80 60 40 45



20 40



74 60



102 80



100



120



Appendix III: Mass Spectra



61



RT: 2.43 AI: 721 KI: 728 Methyl butanoate CAS#: 623-42-7 MF: C5 H10 O2 FW: 102 CN: butanoic acid, methyl ester Synonyms: methyl butyrate Source: Aldrich Chem.



MSD LIB#: 71



O



O-Me



RT: 2.45 AI: 723 KI: 731 Buten-1-ol CAS#: 763-32-6 MF: C5 H10 O FW: 86 MSD LIB#: 326 CN: 3-buten-1-ol, 3-methylSynonyms: 3-isopentyl alcohol; isobutenylcarbinol Source: ref. cpd. ex E. Von Rudloff 100



41



80



56



OH



60



68



40 86



20 60



80



100



120



140



RT: 2.46 AI: 724 KI: 732 Methyl-1-butanol CAS#: 137-32-6 MF: C5 H12 O FW: 88 MSD LIB#: 1638 CN: 1-butanol, 2-methylSynonyms: sec-butylcarbinol Source: Aldrich Chem. 100



56



80



OH



60



70



40 42 20 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



62



RT: 2.50 AI: 728 KI: 737 Methyl-2-pentanone CAS#: 108-10-1 MF: C6 H12 O FW: 100 MSD LIB#: 1707 CN: 2-pentanone, 4-methylSynonyms: isopropyl acetone; hexon; methyl isobutyl ketone; MIBK Source: Aldrich Chem. 100



43 O



80 60 40



57 85



20 60



100



80



100



RT: 2.50 AI: 728 KI: 737 Norbornene CAS#: 498-66-8 MF: C7 H10 FW: 94 CN: bicyclo(2.2.1)hept-2-ene Synonyms: norcamphene; norfenchene Source: ref. cpd. ex E. von Rudloff



120



140



MSD LIB#: 1186



66



100 80 60 40 20



41



79



51 60



80



94 100



RT: 2.53 AI: 731 KI: 740 Isopentyl alcohol CAS#: 123-51-3 MF: C5 H12 O FW: 88 CN: 1-butanol, 3-methylSynonyms: isoamyl alcohol Source: Aldrich Chem. 100



120



140



MSD LIB#: 1431



41 55



80 70



60 40 20 60



80



100



120



140



Appendix III: Mass Spectra



63



RT: 2.54 AI: 732 KI: 742 Thiazole CAS#: 288-47-1 MF: C3 H3 N S FW: 85 CN: thiazole Synonyms: none Source: Aldrich Chem. 58



100



MSD LIB#: 67



85



N



80 S



60 40 20



45 60



80



100



120



140



RT: 2.58 AI: 737 KI: 746 Tiglic aldehyde CAS#: 497-03-0 MF: C5 H8 O FW: 84 MSD LIB#: 1959 CN: 2-butenal, 2-methyl-, (E)Synonyms: tigaldehyde; crotonaldehyde, 2-methyl-,(E)Source: Bedoukian Res. ex JJ Brophy 100



84



55



E O



80 60 40 41 20 60



80



100



RT: 2.61 AI: 740 KI: 750 Methyl cyclohexene CAS#: 591-47-9 MF: C7 H12 FW: 96 CN: cyclohexene, 4-methylSynonyms: none Source: Bedoukian Res.



120



140



MSD LIB#: 2072



81



100 80 60 40



54



67



96



20 41 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



64



RT: 2.65 AI: 744 KI: 754 Penten-1-al CAS#: 1576-87-0 MF: C5 H8 O FW: 84 MSD LIB#: 1967 CN: 2-pentenal, (2E)Synonyms: γ-methyl crotonaldehyde Source: Bedoukian Res. ex JJ Brophy 55



100



O



E



80 60



84 41



40 20



69 60



80



100



120



140



RT: 2.66 AI: 745 KI: 755 Pentanol CAS#: 108-11-2 MF: C6 H14 O FW: 102 MSD LIB#: 2017 CN: 2-pentanol, 4-methylSynonyms: 3-MIC; metilamil alcohol; isobutylmethylcarbinol Source: ref. cpd. ex JJ Brophy 45



100



OH



80 60 40 69



20



84



57 40



60



80



100



120



RT: 2.81 AI: 760 KI: 770 Cyclohexadiene CAS#: 1489-57-2 MF: C7 H10 FW: 94 MSD LIB#: 2199 CN: 1,3-cyclohexadiene, 2-methylSynonyms: dihydrotoluene, 3,4Source: Bedoukian Res. 79



100 80 60



94



40 20



41



66



53 60



80



100



120



140



Appendix III: Mass Spectra



65



RT: 2.81 AI: 761 KI: 770 Isobutyl acetate CAS#: 110-19-0 MF: C6 H12 O2 FW: 116 MSD LIB#: 1607 CN: acetic acid, 2-methylpropyl ester Synonyms: isobutyl ethanoate Source: Aldrich Chem.; 0.01% Anthemis nobilis, Proc. 11th Intl. Cong. Ess. Oils, New Delhi, India 4:207(1989) 43



100 80



O



O



60 40 56



20 40



73 60



80



100



120



140



RT: 2.82 AI: 762 KI: 771 Pentanol CAS#: 71-41-0 MF: C5 H12 O FW: 88 MSD LIB#: 1248 CN: 1-pentanol Synonyms: amyl alcohol Source: Aldrich Chem. ex Art Tucker; 0.60% Brassica juncea, Nippon Noge., Kaishi 54(#2):99(1980); 0.50% Coridotothymus capitatus; 0.50% Psidium guajava 100 80



42 55



60 40



70



20 60



80



RT: 2.83 AI: 763 KI: 772 Butanoic acid CAS#: 107-92-6 MF: C4 H8 O2 FW: 88 CN: butanoic acid Synonyms: butyric acid Source: Bedoukian Res.



100



120



140



MSD LIB#: 2069



O



OH



Adams: Essential Oil Components by GC/MS



66



RT: 2.85 AI: 765 KI: 773 Buten-1-ol CAS#: 556-82-1 MF: C5 H10 O FW: 86 MSD LIB#: 325 CN: 2-buten-1-ol, 3-methylSynonyms: dimethylallyl alcohol; prenol; 3-methylcrotyl alcohol; prenyl alcohol Source: ref. cpds. ex E. von Rudloff 71



100



OH



80 41 60 40



53 86



20 60



80



100



120



140



RT: 2.85 AI: 765 KI: 773 Pentenol CAS#: 1576-95-0 MF: C5 H10 O FW: 86 MSD LIB#: 1250 CN: 2-penten-1-ol, (Z)Synonyms: none Source: Aldrich Chem. ex Art Tucker; 1.07% Spondias cytherea, FFJ 10:375(1994); 0.30% Lawsonia inermis; 0.30% Angelica archangelica (seed) OH



Z



RT: 2.88 AI: 769 KI: 776 Buten-2-ol acetate CAS#: 24509-88-4 MF: C7 H12 O2 FW: 128 MSD LIB#: 324 CN: 3-buten-2-ol, 2-methyl-, acetate Synonyms: dimethylallyl acetate(1,1); dimethylvinylcarbinyl acetate Source: acetylation of buten-2-ol, 2-methyl-3-(5815) 43



100



O-Ac



80 60 40



56



91 73 79



20 40



60



80



100



120



140



Appendix III: Mass Spectra



67



RT: 2.88 AI: 769 KI: 776 Hexen-3-ol CAS#: 4798-44-1 MF: C6 H12 O FW: 100 MSD LIB#: 1948 CN: 1-hexen-3-ol Synonyms: propylvinylcarbinol Source: Bedoukian Res. ex JJ Brophy; 6.07% Psidium guajava, p. 221, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 4.00% Amomum ptycholimatum; 1.17% Jasminum officinale 57



100 80



OH



60 40 20 43



72 60



80



100



120



140



RT: 2.90 AI: 771 KI: 778 Cyclohexadiene CAS#: 1489-56-1 MF: C7 H10 FW: 94 MSD LIB#: 2200 CN: 1,3-cyclohexadiene, 1-methylSynonyms: dihydrotoluene, 2,3Source: Bedoukian Res. 79



100 80 60



94



40 20



51



65 60



80



100



120



140



RT: 2.97 AI: 778 KI: 784 Methyl-2-butenal CAS#: 107-86-8 MF: C5 H8 O FW: 84 MSD LIB#: 1640 CN: 2-butenal, 3-methylSynonyms: Senecioaldehyde, crotonaldehyde, prenal Source: Aldrich Chem. 100



41



84



55



O



80 60 40 20



69 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



68



RT: 3.03 AI: 785 KI: 789 Butanediol CAS#: 513-85-9 MF: C4 H10 O2 FW: 90 MSD LIB#: 322 CN: 2,3-butanediol Synonyms: 2,3-butylene glycol; dimethylethylene glycol Source: Fluka ex Art Tucker; 0.01% Jasminum officinale (absolute), J. Agric. Food Chem. 31:558(1985) 45



100 80 60 40 20



57 60



80



100



120



140



RT: 3.03 AI: 785 KI: 789 Cyclohexene CAS#: 1888-90-0 MF: C7 H10 FW: 94 MSD LIB#: 2201 CN: cyclohexene, 3-methyleneSynonyms: methylene cyclohexene, 3Source: Bedoukian Res. 79



100 80 60



94



40 20



41



66



53 60



80



RT: 3.04 AI: 786 KI: 790 Cyclopentanol CAS#: 96-41-3 MF: C5 H10 O FW: 86 CN: cyclopentanol Synonyms: hydrocyclopentane Source: Fluka Chem. ex Art Tucker



100



120



MSD LIB#: 539



140



Appendix III: Mass Spectra



69



RT: 3.05 AI: 787 KI: 790 Butanethiol, 2-methylCAS#: 1878-18-8 MF: C5 H12 S FW: 104 MSD LIB#: 1702 CN: 1-butanethiol, 2-methylSynonyms: none Source: Aldrich Chem. 100



41 HS



80 60 55



47



40



70



104



20 40



60



80



100



120



RT: 3.06 AI: 788 KI: 791 Dimethyl-3-pentanone CAS#: 565-80-0 MF: C7 H14 O FW: 114 MSD LIB#: 2007 CN: 3-pentanone, 2,4-dimethylSynonyms: isobutyrone; isopropyl ketone; disopropyl ketone Source: Aldrich Chem. ex JJ Brophy 43



100



O



80 60 71



40 20



114 40



60



80



100



120



RT: 3.06 AI: 788 KI: 791 Isopentyl formate CAS#: 110-45-2 MF: C6 H12 O2 FW: 116 MSD LIB#: 872 CN: 1-butanol, 3-methyl-, formate Synonyms: isoamyl formate; isoamyl methanoate; isopentyl methanoate Source: Aldrich Chem. 55



100



O



80 60



41



70



40 20 40



60



80



100



120



140



O



Adams: Essential Oil Components by GC/MS



70



RT: 3.06 AI: 788 KI: 791 Octene CAS#: 111-66-0 MF: C8 H16 FW: 112 MSD LIB#: 1213 CN: octene (1-) Synonyms: caprylene Source: ref. cpd. ex E. von Rudloff; 0.20% Artemisia absinthum, Z. Naturforsch. 36c:369(1981) 100



41 55



80 70



60 40



83



20



112 40



60



80



100



120



RT: 3.08 AI: 790 KI: 793 Isopropyl isobutyrate CAS#: 617-50-5 MF: C7 H14 O2 FW: 130 MSD LIB#: 1621 CN: propanoic acid, 2-methyl-, 1-methylethyl ester Synonyms: isobutyric acid, isopropyl ester Source: Aldrich Chem.; 0.29% Passiflora edulis, p. 220, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.02% Ruta chalapensis



O



O



RT: 3.10 AI: 792 KI: 794 Hexenal CAS#: 69112-21-6 MF: C6 H10 O FW: 98 MSD LIB#: 1975 CN: 3-hexenal, (3E)Synonyms: trans-3-hexenal Source: Bedoukian Res. ex JJ Brophy; 0.43% Psidium guajava, FFJ 6:143(1991); 0.01% Salvia officinalis 100



41 E



80



O



60 40



69 55 80



20 60



80



98 100



120



140



Appendix III: Mass Spectra



71



RT: 3.14 AI: 796 KI: 797 Hexanol CAS#: 626-93-7 MF: C6 H14 O FW: 102 CN: 2-hexanol Synonyms: sec-hexyl alcohol Source: alcohols mix (2-OHs) ex K-H Kubeczka



MSD LIB#: 1814



OH



RT: 3.15 AI: 797 KI: 798 Hexenal CAS#: 6789-80-6 MF: C6 H10 O FW: 98 MSD LIB#: 2057 CN: 3-hexenal,(3Z)Synonyms: hexenal, cis-3Source: Bedoukian Res.; 0.83% Bouea macrophylla, JEOR 8:99(1996); 0.30% Psidium guajava 100



41 Z



80



O



60 40



69



55



83



20 60



98



80



100



120



140



RT: 3.17 AI: 800 KI: 800 Hexanedione CAS#: 4437-51-8 MF: C6 H10 O2 FW: 114 MSD LIB#: 800 CN: 3,4-hexanedione Synonyms: bipropionyl Source: Aldrich Chem. ex Art Tucker 57



100



O



80 60 40



O



20



114 40



60



80



100



120



Adams: Essential Oil Components by GC/MS



72



RT: 3.17 AI: 800 KI: 800 Octane CAS#: 111-65-9 MF: C8 H18 FW: 114 CN: octane Synonyms: none Source: ref. cpd. ex E. von Rudloff



MSD LIB#: 87



43



100



CH3(CH2)6CH3



80 60 40



85



57 71



20



114 40



60



80



100



120



RT: 3.19 AI: 801 KI: 801 Hexanal CAS#: 66-25-1 MF: C6 H12 O FW: 100 MSD LIB#: 799 CN: hexanal Synonyms: caproaldehyde Source: ref. cpd. ex E. von Rudloff; 14.88% Pyrus serotina (Asian), JEOR 4:645(1992); 3.37% Spondias cytherea; 2.97% Psidium guajava 100



44 H



80



56



O



60 40 72



20 60



82 80



100



RT: 3.20 AI: 801 KI: 802 Octene CAS#: 14850-23-8 MF: C8 H16 FW: 112 CN: 4-octene, (E)Synonyms: none Source: ref. cpd. ex E. von Rudloff 100



41



120



140



MSD LIB#: 1209



55 E



80 60 40



70



112



83



20 40



60



80



100



120



Appendix III: Mass Spectra



73



RT: 3.22 AI: 802 KI: 804 Ethyl butanoate CAS#: 105-54-4 MF: C6 H12 O2 FW: 116 CN: butanoic acid, ethyl ester Synonyms: ethyl butyrate Source: Aldrich Chem.



MSD LIB#: 77



O



O



RT: 3.25 AI: 804 KI: 806 Methyl-1,4-cyclohexadiene CAS#: 4313-57-9 MF: C7 H10 FW: 94 MSD LIB#: 1705 CN: 1,4-cyclohexadiene, 1-methylSynonyms: dihydrotoluene Source: Aldrich Chem. 79



100 80 60 40



94



51



63



20 41 60



80



100



120



140



RT: 3.30 AI: 807 KI: 810 Norbornene CAS#: 694-91-7 MF: C8 H10 FW: 106 MSD LIB#: 1183 CN: bicyclo(2.2.1)hept-2-ene, 5-methyleneSynonyms: none Source: ref. cpd. ex E. von Rudloff 66



100



91



80 60



78



40



106



51



20 40



60



80



100



120



Adams: Essential Oil Components by GC/MS



74



RT: 3.31 AI: 807 KI: 811 Butyl acetate CAS#: 123-86-4 MF: C6 H12 O2 FW: 116 MSD LIB#: 23 CN: acetic acid, butyl ester Synonyms: butyl ethanoate Source: alcohols mix ex E. von Rudloff; 53.06% Michelia figo (flower), p. 17, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 22.24% Artabotrys hexapetalus (flower); 9.08% Mandragora officinarum 43



100 80 60 40



56



20



73 40



60



80



100



RT: 3.32 AI: 808 KI: 811 Octene CAS#: 7642-04-8 MF: C8 H16 FW: 112 CN: 2-octene, (Z)Synonyms: none Source: ref. cpd. ex E. von Rudloff 100



41



120



140



MSD LIB#: 1207



55 Z



80



(CH2)4-CH3



60 70



40



112



83



20 40



60



80



100



120



RT: 3.42 AI: 814 KI: 819 Thiazole CAS#: 693-95-8 MF: C4 H5 N S FW: 99 MSD LIB#: 59 CN: thiazole, 4-methylSynonyms: none Source: Aldrich Chem. 71



100



99



N



80 60



S



45



40 20 60



80



100



120



140



Appendix III: Mass Spectra



75



RT: 3.45 AI: 815 KI: 821 Octene CAS#: 13389-42-9 MF: C8 H16 FW: 112 CN: 2-octene, (E)Synonyms: none Source: ref. cpd. ex E. von Rudloff 100



41



MSD LIB#: 1208



55



80 60 70



40



112



83



20 40



60



80



100



120



RT: 3.52 AI: 819 KI: 826 Pyrazine CAS#: 109-08-0 MF: C5 H6 N2 FW: 94 MSD LIB#: 57 CN: pyrazine, methylSynonyms: none Source: Aldrich Chem. 94



100



N



80 67



60



N



40 20



42



53 60



80



100



120



140



RT: 3.55 AI: 821 KI: 828 Methyl pentanoate CAS#: 624-24-8 MF: C6 H12 O2 FW: 116 MSD LIB#: 1106 CN: pentanoic acid, methyl ester Synonyms: methyl valerate Source: CTC Chem. ex Art Tucker; 0.22% Aglaia duperreana (flower), p. 75, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.01% Spartium junceum Me-O



O



Adams: Essential Oil Components by GC/MS



76



RT: 3.60 AI: 824 KI: 831 Cyclohexene CAS#: 503-45-7 MF: C9 H16 FW: 124 MSD LIB#: 2202 CN: cyclohexene, 3,3,5-trimethylSynonyms: cyclogeraniolene, epsilonSource: Bedoukian Res. 109



100 67



80 60



82 95



40 41



124



55



20 40



60



80



100



RT: 3.62 AI: 825 KI: 832 Prenyl formate CAS#: 68480-28-4 MF: C6 H10 O2 FW: 114 CN: 2-buten-1-ol, 3-methyl-, formate Synonyms: none Source: Bedoukian Res.



120



140



MSD LIB#: 2050



O



O



RT: 3.66 AI: 827 KI: 835 Isovaleric acid CAS#: 503-74-2 MF: C5 H10 O2 FW: 102 CN: butanoic acid, 3-methylSynonyms: isopentanoic acid; 3-methylbutanoic acid Source: Valeriana officinalis root oil ex Art Tucker



MSD LIB#: 1531



60



100



O



80 60 40



OH



41



20



87



69 40



60



80



100



120



Appendix III: Mass Spectra



77



RT: 3.67 AI: 828 KI: 836 Furfural CAS#: 98-01-1 MF: C5 H4 O2 FW: 96 MSD LIB#: 725 CN: 2-furancarboxaldehyde Synonyms: α-furole; artificial ant oil; 2-formylfuran Source: Aldrich Chem.; 72.39% Tamarindus indica, JEOR 2:197(1990); 19.10% Averrhoa bilimbi (fruit); 5.30% Zizyphus jujuba (fruit) 96



100



O



80



O



60 40 20 42



67



50 60



80



100



120



140



RT: 3.70 AI: 830 KI: 838 Pentanol CAS#: 626-89-1 MF: C6 H14 O FW: 102 MSD LIB#: 1249 CN: 1-pentanol, 4-methylSynonyms: none Source: Aldrich Chem. ex Art Tucker



OH



RT: 3.72 AI: 831 KI: 839 Pentanone CAS#: 123-42-2 MF: C6 H12 O2 FW: 116 MSD LIB#: 1750 CN: 2-pentanone, 4-hydroxy-4-methylSynonyms: diacetone Source: Aldrich Chem. 43



100



O



80 60 59



40



101



20 40



60



80



100



120



140



OH



Adams: Essential Oil Components by GC/MS



78



RT: 3.74 AI: 832 KI: 840 Cyclohexene CAS#: 933-12-0 MF: C9 H16 FW: 124 MSD LIB#: 2203 CN: cyclohexene, 3,5,5-trimethylSynonyms: cyclogeraniolene, δSource: Bedoukian Res. 68



100 80



109



60 40 41 20 40



124



81



53 60



95



80



100



120



140



RT: 3.75 AI: 832 KI: 841 Butanoic acid CAS#: 116-53-0 MF: C5 H10 O2 FW: 102 MSD LIB#: 1966 CN: butanoic acid, 2-methylSynonyms: 2-methylbutyric acid Source: Bedoukian Res. ex JJ Brophy 74



100



OH



80 60 40



O



41



57 87



20 40



60



80



100



120



RT: 3.76 AI: 833 KI: 841 Pentanol CAS#: 589-35-5 MF: C6 H14 O FW: 102 MSD LIB#: 1987 CN: 1-pentanol, 3-methylSynonyms: 2-ethyl-4-butanol Source: Bedoukian Res. ex JJ Brophy 56



100



OH



80 60



69



41



40 84



20 40



60



80



100



120



Appendix III: Mass Spectra



79



RT: 3.81 AI: 836 KI: 844 Isopropyl butanoate CAS#: 638-11-9 MF: C7 H14 O2 FW: 130 MSD LIB#: 335 CN: butanoic acid, 1-methylethyl ester Synonyms: isopropyl butyrate Source: Aldrich Chem.



O



O



RT: 3.96 AI: 844 KI: 853 Hexenol CAS#: 928-97-2 MF: C6 H12 O FW: 100 MSD LIB#: 806 CN: 3-hexen-1-ol, (E)Synonyms: trans-3-hexenol Source: ref. cpd. ex E. von Rudloff; 5.12% Lawsonia inermis, p. 44, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.85% Psidium guajava; 0.10% Narcissus tazetta (absolute) E



OH



RT: 3.99 AI: 846 KI: 855 Hexenal CAS#: 6728-26-3 MF: C6 H10 O FW: 98 MSD LIB#: 802 CN: 2-hexenal, (E)Synonyms: trans-2-hexenal; leaf aldehyde Source: Aldrich Chem. ex Art Tucker; 33.11% Spondias cytherea, FFJ 10:375(1995); 19.50% Comptonia peregrina; 10.00% Camellia sinensis 100 80



41 O



55



60



E



69 83



40 20



98 60



80



100



120



140



H



Adams: Essential Oil Components by GC/MS



80



RT: 4.01 AI: 847 KI: 856 Salvene CAS#: 33746-70-2 MF: C9 H16 FW: 124 MSD LIB#: 1374 CN: 2-heptene, 6-methyl-5-methylene-, (Z)Synonyms: cis-salvene Source: Salvia officinalis oil ex Art Tucker; 0.75% Salvia officinalis, JEOR 2:139(1990); 0.24% Artemisia absinthum Z



RT: 4.04 AI: 849 KI: 858 Ethyl isovalerate CAS#: 108-64-5 MF: C7 H14 O2 FW: 130 MSD LIB#: 675 CN: butanoic acid, 3-methyl-, ethyl ester Synonyms: ethyl isopentanoate; ethyl 3-methylbutnoate Source: ref. cpd. ex Z. Fleisher; 0.86% Artemisia judaica, JEOR 2:271(1990); 0.12% Chamomilla recutita; 0.01% Calamintha nepeta 88



100 80 41



57



O



60



O



70



40 20



115 130 40



60



80



100



120



140



RT: 4.06 AI: 850 KI: 859 Hexenol CAS#: 928-96-1 MF: C6 H12 O FW: 100 MSD LIB#: 805 CN: hex-3-en-1-ol, (Z)Synonyms: cis-3-hexenol; leaf alcohol Source: ref. cpd. ex E. von Rudloff; 13.00% Lawsonia inermis (flower), JEOR 7:425(1995); 10.64% Convallaria majalis; 10.39% Nicotiana rustica (flower) Z



OH



Appendix III: Mass Spectra



81



RT: 4.13 AI: 854 KI: 862 Hexenol CAS#: 928-95-0 MF: C6 H12 O FW: 100 MSD LIB#: 1947 CN: (2E)-hexen-1-ol Synonyms: hexenol, trans-2Source: Bedoukian Res. ex JJ Brophy; 7.86% Spondias cytherea, FFJ 10:375(1995); 6.10% Thymus vulgarius; 3.22% Lawsonia inermis E OH



RT: 4.20 AI: 858 KI: 866 Pentenoic acid CAS#: 591-80-0 MF: C5 H8 O2 FW: 100 MSD LIB#: 1969 CN: 4-pentenoic acid Synonyms: 4-pentenoic acid Source: Bedoukian Res. ex JJ Brophy; 0.81% Gardenia jasminoides, JEOR 8:241(1996) 55



100



OH



80 60



O



41



40



100



20



73 60



82 80



100



120



140



RT: 4.20 AI: 858 KI: 866 Salvene CAS#: 33746-69-9 MF: C9 H16 FW: 124 MSD LIB#: 1375 CN: 2-heptene, 6-methyl-5-methylene-, (E)Synonyms: trans-salvene Source: Salvia officinalis oil ex Art Tucker; 0.35% Salvia officinalis, Deut. Apoth. Ztg. 127:2543(1987); 0.10% Thuja occidentalis



E



Adams: Essential Oil Components by GC/MS



82



RT: 4.22 AI: 859 KI: 867 Hexenol CAS#: 928-94-9 MF: C6 H12 O FW: 100 MSD LIB#: 1945 CN: 2-hexen-1-ol,(Z)Synonyms: none Source: Bedoukian Res. ex JJ Brophy; 0.10% Lawsonia inermis, JEOR 7:425(1995); 0.01% Daphne genkwa; 0.01% Calamintha nepeta 57



100



HO



80 60 40



Z



41 67



82



20 60



80



100



RT: 4.28 AI: 863 KI: 870 Hexanol CAS#: 111-27-3 MF: C6 H14 O FW: 102 CN: hexan-1-ol Synonyms: none Source: ref. cpd. ex E. von Rudloff



120



140



MSD LIB#: 1429



RT: 4.28 AI: 863 KI: 870 Methyl tiglate CAS#: 6622-76-0 MF: C6 H10 O2 FW: 114 MSD LIB#: 41 CN: 2-butenoic acid, 2-methyl-, methyl ester Synonyms: crotonic acid, 2-methyl, methyl ester Source: Aldrich Chem.; 3.29% Gardenia jasminoides, p. 90, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.12% Chamomilla recutita 55



100



O



80 60



83



O-Me



114



40 20



99



43 40



60



80



100



120



Appendix III: Mass Spectra



83



RT: 4.40 AI: 869 KI: 876 Isopentyl acetate CAS#: 123-92-2 MF: C7 H14 O2 FW: 130 MSD LIB#: 1866 CN: 1-butanol, 3-methyl-, acetate Synonyms: banana oil, isoamyl acetate, pear oil, isopentyl ethanoate Source: Aldrich Chem. 43



100 80 60



OAc



70



55



40 20



61 40



87



60



80



100



120



140



RT: 4.40 AI: 869 KI: 876 Methyl-(3Z)-hexen-2-one CAS#: 1669-43-8 MF: C7 H12 O FW: 112 MSD LIB#: 2025 CN: 3-hexen-2-one, 5-methyl- (3Z)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 43



100



O



80



Z



60



97



69



40 20



112



55 40



60



80



RT: 4.42 AI: 871 KI: 877 Hexenol CAS#: 928-91-6 MF: C6 H12 O FW: 100 CN: 4-hexen-1-ol, (4Z)Synonyms: none Source: Bedoukian Res.



100



120



MSD LIB#: 2047



OH



Z



Adams: Essential Oil Components by GC/MS



84



RT: 4.42 AI: 871 KI: 877 Methyl pentanoate CAS#: 2177-77-7 MF: C7 H14 O2 FW: 130 MSD LIB#: 1970 CN: pentanoic acid, 2-methyl-, methyl ester Synonyms: Valeric acid, 2-methyl, methyl ester Source: Bedoukian Res. ex JJ Brophy O



O



RT: 4.50 AI: 875 KI: 881 Methyl butyl acetate CAS#: 624-41-9 MF: C7 H14 O2 FW: 130 MSD LIB#: 1088 CN: 1-butanol, 2-methyl, acetate Synonyms: sec-pentyl acetate; sec-amyl acetate Source: Aldrich Chem.; 4.24% Michelia figo, p. 17, in: Aromatic Plants & Essential Oil Constituents, Peace Book Co., Hong Kong(1993); 2.80% Michelia balansae; 0.62% Anthemis nobilis 43



100



O-Ac



80 60 40



70 55



20 40



60



80



100



120



140



RT: 4.59 AI: 880 KI: 885 Buten-1-ol acetate CAS#: 5205-07-2 MF: C7 H12 O2 FW: 128 MSD LIB#: 320 CN: 3-buten-1-ol, 3-methyl, acetate Synonyms: 3-methyl-3-butenyl acetate Source: acetylation of 3-me-1-buten-1-ol(6284) 43



100 80



O-Ac



60 68



40 20



53 40



60



80



100



120



140



Appendix III: Mass Spectra



85



RT: 4.59 AI: 880 KI: 885 Isopropyl 2-methylbutyrate CAS#: 66576-71-4 MF: C8 H16 O2 FW: 144 MSD LIB#: 1623 CN: butanoic acid, 2-methyl-, 1-methylethyl ester Synonyms: none Source: Aldrich Chem. 43



100



O



57



80



O



60 85



40



103



74



20



116 129



40



60



80



100



120



RT: 4.60 AI: 881 KI: 885 Allyl butanoate CAS#: 2051-78-7 MF: C7 H12 O2 FW: 128 CN: butanoic acid, 2-propenyl ester Synonyms: 2-propenyl butyrate Source: Aldrich Chem.



MSD LIB#: 72



71



43



100



140



O



80 60



O



40 20



57 40



60



80



100



120



140



RT: 4.60 AI: 881 KI: 885 Butenoic acid CAS#: 541-47-9 MF: C5 H8 O2 FW: 100 MSD LIB#: 1704 CN: 2-butenoic acid, 3-methylSynonyms: Crotonic acid , senecioic acid Source: Aldrich Chem. 100



100 80



O



60 40 20



55



OH



82



41



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



86



RT: 4.65 AI: 884 KI: 888 Ethyl pent-4-enoate CAS#: 1968-40-7 MF: C7 H12 O2 FW: 128 MSD LIB#: 678 CN: 4-pentenoic acid, ethyl ester Synonyms: 4-ethoxycarbonylbut-1-ene Source: Bedoukian Res. ex Art Tucker 55



100



O



80 60



O



40 20



83



41



69



40



128



60



80



100



120



140



RT: 4.66 AI: 884 KI: 888 Santene CAS#: 529-16-8 MF: C9 H14 FW: 122 MSD LIB#: 1 CN: bicyclo(2.2.1)hept-2-ene, 2,3-dimethylSynonyms: none Source: Abies siberica oil ex E. von Rudloff; 6.10% Bupleurum linearifolium, Pakistan J. Sci. Ind. Res. 22:325(1979); 5.00% Abies alba; 3.46% Pseudotsuga menziesii 79



100



94



80 60 40 20 41



122 51



65



40



107



60



80



100



RT: 4.68 AI: 885 KI: 889 Heptanol CAS#: 589-55-9 MF: C7 H16 O FW: 116 CN: 4-heptanol Synonyms: dipropylcarbinol Source: Pfaltz & Bauer ex Art Tucker



120



140



MSD LIB#: 782



55



100



OH



80 73



60 43



40 20 40



60



80



100



120



140



Appendix III: Mass Spectra



87



RT: 4.70 AI: 886 KI: 890 Pentanal CAS#: 4221-03-8 MF: C5 H10 O2 FW: 102 MSD LIB#: 1246 CN: pentanal, 5-hydroxySynonyms: valeraldehyde, 5-hydroxySource: ref. cpd. ex E. von Rudloff 100



41



56



O



80 H



60



OH



40 101



20



74 40



60



80



100



120



RT: 4.74 AI: 889 KI: 892 Heptanone CAS#: 110-43-0 MF: C7 H14 O FW: 114 MSD LIB#: 786 CN: 2-heptanone Synonyms: methylamyl ketone; amyl methyl ketone; pentyl methyl ketone; methyl pentyl ketone; Source: Aldrich Chem.; 0.30% Sclerua striatinux (rhizome), JEOR 8:59(1996); 0.10% Zingiber officinale; 0.05% Boldea fragrans (leaf) 43



100 80



58



60 40



71



20 40



60



114 80



100



120



RT: 4.80 AI: 892 KI: 894 Methyl-(3E)-hexen-2-one CAS#: 1821-29-0 MF: C7 H12 O FW: 112 MSD LIB#: 2024 CN: 3-hexen-2-one, 5-methyl-, (3E)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 43



100



O



80



E



60



97



69



40 20



112



55 40



60



80



100



120



Adams: Essential Oil Components by GC/MS



88



RT: 4.82 AI: 893 KI: 895 Heptenal CAS#: 6728-31-0 MF: C7 H12 O FW: 112 CN: 4-heptenal, (Z)Synonyms: none Source: Bedoukian Res. ex JJ Brophy



MSD LIB#: 1985



Z O



RT: 4.84 AI: 894 KI: 896 Heptanol CAS#: 543-49-7 MF: C7 H16 O FW: 116 MSD LIB#: 1815 CN: 2-heptanol Synonyms: sec-heptyl alcohol Source: alcohols mix (2-OHs) ex K-H Kubeczka; 0.80% Curcuma aromatica, JEOR 8:633(1996); 0.70% Lawsonia inermis (flower); 0.60% Aframomum melegueta OH



RT: 4.86 AI: 896 KI: 897 Pyrazine CAS#: 3149-28-8 MF: C5 H6 N2 O FW: 110 MSD LIB#: 58 CN: pyrazine, methoxySynonyms: none Source: Aldrich Chem. 110



100



N



80 60



20



68



53



40



80



41 40



N



95 60



80



100



120



O-Me



Appendix III: Mass Spectra



89



RT: 4.91 AI: 898 KI: 899 Propyl butanoate CAS#: 105-66-8 MF: C7 H14 O2 FW: 130 CN: butanoic acid, propyl ester Synonyms: propyl butryate; butyric acid, propyl ester Source: Aldrich Chem.



MSD LIB#: 336



O



O



RT: 4.93 AI: 900 KI: 900 Nonane CAS#: 111-84-2 MF: C9 H20 FW: 128 MSD LIB#: 88 CN: nonane Synonyms: none Source: ref. cpd. ex E. von Rudloff; 42.00% Pittosporum tobira, p. 57, in: Prog. in Ess. Oil Research, E.-J. Brunke Ed., Gruyter Publ., Berlin(1986); 9.70% Hypericum perforatum; 1.28% Coriandrum sativum 43



100



57



80 60 40



85



71



20 40



60



99 80



100



128 120



140



RT: 4.96 AI: 901 KI: 901 Ethyl pentanoate CAS#: 539-82-2 MF: C7 H14 O2 FW: 130 MSD LIB#: 78 CN: pentanoic acid, ethyl ester Synonyms: ethyl valerate Source: Aldrich Chem.; 1.38% Pyrus serotina (Asian), JEOR 4:645(1992); 0.10% Tagetes minuta 88



100



60



O



57



80 41



O



40



73



101



20 130 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



90



RT: 4.97 AI: 901 KI: 901 Propanal CAS#: 3268-49-3 MF: C4 H8 OS FW: 104 MSD LIB#: 1709 CN: 1-propanal, 3-(methylthio)Synonyms: methional, thiapentanal Source: Aldrich Chem. 48



100 80



O



S



60 76



61



40



104



20 40



60



80



100



120



RT: 4.98 AI: 901 KI: 902 Heptanal CAS#: 111-71-7 MF: C7 H14 O FW: 114 MSD LIB#: 779 CN: heptanal Synonyms: enanthaldehyde; enanthole; oennathal Source: Pfaltz & Bauer ex Art Tucker; 17.07% Michelia champaca, p. 16, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 14.85% Narcissus tazetta; 1.80% Tilia cordata



RT: 5.03 AI: 903 KI: 904 Ethoxy ethyl acetate CAS#: 111-15-9 MF: C6 H12 O3 FW: 132 MSD LIB#: 1749 CN: 2-ethoxyethyl acetate Synonyms: cellusolve acetate, ethyl glycol acetate Source: Baker Chem. 43



100



O



80



O O



60 40 59



20 40



60



72 87 80



100



120



140



Appendix III: Mass Spectra



91



RT: 5.05 AI: 904 KI: 905 Hydroxybutanoic acid lactone CAS#: 96-48-0 MF: C4 H6 O2 FW: 86 MSD LIB#: 1596 CN: 2(3H)-furanone, dihydroSynonyms: 4-butanolide, butyryl lactone, butyric acid lactone Source: Aldrich Chem. 100



42 O



80 60



O



40 56



20



86 60



80



100



120



140



RT: 5.12 AI: 906 KI: 908 Santolina triene CAS#: 2153-66-4 MF: C10 H16 FW: 136 MSD LIB#: 226 CN: 1,4-hexadiene, 3-ethenyl-2,5-dimethylSynonyms: none Source: Artemisia tridentata, SLC, Utah, RP Adams #5577; 1.40% Santolina chamaecyparissus, Sci. Pharm. 55:267(1987); 0.40% Ormenis mixta; 0.36% Artemisia vestita 93



100 80



79



60 41 40



121



67 105



55



20



136 40



60



80



100



120



140



RT: 5.13 AI: 907 KI: 909 Butyl propanoate CAS#: 590-01-2 MF: C7 H14 O2 FW: 130 MSD LIB#: 331 CN: propanoic acid, butyl ester Synonyms: UN 1914 Source: Aldrich Chem.; 0.17% Citrus sinensis, JEOR 7:105(1995); 0.01% Lavender angustifolia; 0.01% Spartium junceum 57



100



O



80 60 40



O



75



41



20 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



92



RT: 5.14 AI: 907 KI: 909 Hexadienal CAS#: 142-83-6 MF: C6 H8 O FW: 96 MSD LIB#: 798 CN: 2,4-hexadienal, (E,E)Synonyms: sorbaldehyde; trans-2, trans-4-hexadienal Source: ref. cpd. ex E. von Rudloff 81



100



O



80



E



60 41



53



67



40



E



96



20 60



80



100



120



140



RT: 5.18 AI: 908 KI: 911 Isobutyl isobutyrate CAS#: 97-85-8 MF: C8 H16 O2 FW: 144 MSD LIB#: 1615 CN: propanoic acid, 2-methyl-, 2-methylpropyl ester Synonyms: isobutyric acid, isobutyl ester Source: Aldrich Chem.; 26.89% Artabotrys hexapetalus, p. 21, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 14.00% Eriocephalus punctualis; 12.70% Anthemis nobilis 100



43



71



80



O



60



57 O



40



89



20



101 40



60



80



100



120



140



RT: 5.18 AI: 908 KI: 911 Pyrazine CAS#: 123-32-0 MF: C6 H8 N2 FW: 108 MSD LIB#: 61 CN: pyrazine, 2,5-dimethylSynonyms: none Source: Aldrich Chem. 100



42 N



80



108



60 N



40 20



81



52 40



60



80



100



120



Appendix III: Mass Spectra



93



RT: 5.19 AI: 909 KI: 912 Acetylfuran CAS#: 1192-62-7 MF: C6 H6 O2 FW: 110 MSD LIB#: 47 CN: ethanone, 1-(2-furanyl)Synonyms: α-acetylfuran, 2-furyl methyl ketone Source: Aldrich Chem.; 0.72% Tamarindus indica, JEOR 2:197(1990); 0.53% Daphne genkwa; 0.18% Gardenia jasminoides 95



100 80 60 40



110



43



20



67



51 40



60



80



100



RT: 5.20 AI: 909 KI: 912 Tiglic acid CAS#: 80-59-1 MF: C5 H8 O2 FW: 100 CN: 2-butenoic acid, 2-methyl-(2E)Synonyms: crotonic acid, trans-2-methyl-; cevadic acid Source: Bedoukian Res. 55



100



120



MSD LIB#: 2061



100



80



O



E



60 40 20



OH



85



45 60



80



100



120



140



RT: 5.21 AI: 909 KI: 912 Pyrazine CAS#: 108-50-9 MF: C6 H8 N2 FW: 108 MSD LIB#: 62 CN: pyrazine, 2,6-dimethylSynonyms: none Source: Aldrich Chem. 100



42



108



N



80 60 N



40 20



67 40



60



81 80



100



Adams: Essential Oil Components by GC/MS



94



RT: 5.25 AI: 911 KI: 914 Amyl acetate CAS#: 628-63-7 MF: C7 H14 O2 FW: 130 MSD LIB#: 128 CN: acetic acid, pentyl ester Synonyms: pentyl acetate; banana oil; birnenoel; pear oil Source: local dry cleaner store 43



100 80 60 40 20



70



61



55 40



60



80



100



120



140



RT: 5.29 AI: 912 KI: 916 Hexadienol CAS#: 17102-64-6 MF: C6 H10 O FW: 98 MSD LIB#: 2098 CN: 2,4-hexadien-1-ol, (2E,4E)Synonyms: sorbic alcohol; sorbinol; trans-trans-2,4-hexadienol Source: Bedoukian Res. 100



41



55 E



80



HO



83



60



98



69



40 20 60



80



100



120



140



RT: 5.29 AI: 912 KI: 916 Pyrazine CAS#: 13925-00-3 MF: C6 H8 N2 FW: 108 MSD LIB#: 54 CN: pyrazine, ethylSynonyms: ethylpyrazine Source: Aldrich Chem. 107



100 80 60 40 20



80



53 41 40



60



80



100



120



E



Appendix III: Mass Spectra



95



RT: 5.29 AI: 912 KI: 916 Tetrahydrofuran CAS#: 104188-15-0 MF: C9 H14 O FW: 138 MSD LIB#: 228 CN: furan, 2,5-diethenyltetrahydro-2-methylSynonyms: none Source: Artemisia tridentata, SLC, Utah, RP Adams #5577 O



RT: 5.32 AI: 913 KI: 917 Anisole CAS#: 100-66-3 MF: C7 H8 O FW: 108 MSD LIB#: 171 CN: benzene, methoxySynonyms: phenyl methyl ether; phenoxymethane Source: Aldrich Chem.; 0.60% Tuber melanosporum, JEOR 1:281(1989); 0.26% Aquilaria agallacho; 0.22% Gardenia jasminoides 108



100



OCH3



65



80



78



60 40 51



20 40



93 60



80



100



120



RT: 5.32 AI: 913 KI: 917 Hexenyl formate CAS#: 33467-73-1 MF: C7 H12 O2 FW: 128 MSD LIB#: 1586 CN: 3-hexen-1-ol, formate, (Z)Synonyms: cis-3-hexenyl formate Source: Aldrich Chem.; 1.20% Viola odorata, Phytochem. 31:571(1992); 0.11% Citrus reticulata; 0.11% Hyacinthus orientalis 67



100 80 60 40



O



41 82



20



55 40



60



80



100



120



O



Z



Adams: Essential Oil Components by GC/MS



96



RT: 5.35 AI: 914 KI: 919 Buten-1-ol, 3-methyl-2-, acetate CAS#: 1191-16-8 MF: C7 H12 O2 FW: 128 MSD LIB#: 1712 CN: 2-buten-1-ol, 3-methyl-, acetate Synonyms: prenyl acetate, dimethylallyl acetate Source: Aldrich Chem. 43



100



O



80 60



67



53



40 20



86 40



60



128



80



100



120



140



RT: 5.38 AI: 915 KI: 920 Pyrazine CAS#: 5910-89-4 MF: C6 H8 N2 FW: 108 MSD LIB#: 60 CN: pyrazine, 2,3-dimethylSynonyms: none Source: Aldrich Chem. 67



100



108



N



80 60



N



40



42



20



52 40



60



80



100



120



RT: 5.46 AI: 918 KI: 923 Heptanone CAS#: 626-33-5 MF: C8 H16 O FW: 128 MSD LIB#: 783 CN: 4-heptanone, 2-methylSynonyms: isobutyl propyl ketone Source: ref. cpd. ex CA McDaniel 100



43



57



80 71



60



85



40 128



20



113 40



60



80



100



120



140



O



Appendix III: Mass Spectra



97



RT: 5.46 AI: 918 KI: 923 Heptanone (impure) CAS#: 15726-15-5 MF: C8 H16 O FW: 128 MSD LIB#: 784 CN: 4-heptanone, 3-methylSynonyms: none Source: ref. cpd. ex CA McDaniel 100



57



43



O



80 71



60



85



40 128



20



113 40



60



80



100



120



RT: 5.46 AI: 918 KI: 923 Hexenyl formate CAS#: 53398-78-0 MF: C7 H12 O2 FW: 128 MSD LIB#: 1984 CN: 2-hexen-1-ol, formate, (2E)Synonyms: trans-2-hexenyl formate Source: Bedoukian Res. ex JJ Brophy 100 80



67 41



E



57 82



60 40 20



99 128 40



60



80



100



RT: 5.46 AI: 918 KI: 923 Isocitronellene CAS#: 85006-04-8 MF: C10 H18 FW: 138 CN: 1,6-octadiene, 5,7-dimethylSynonyms: none Source: Aldrich Chem.



80 60



120



140



MSD LIB#: 861



55



100



83



41



40



67



95



20



123 40



O O



60



80



100



120



138 140



Adams: Essential Oil Components by GC/MS



98



RT: 5.48 AI: 919 KI: 924 Acetonyl acetone CAS#: 110-13-4 MF: C6 H10 O2 FW: 114 CN: 2,5-hexanedione Synonyms: none Source: Fluka Chem. ex Art Tucker



MSD LIB#: 8



O



O



RT: 5.53 AI: 921 KI: 926 Ethyl 2-methyl-4-pentenoate CAS#: 53399-81-8 MF: C8 H14 O2 FW: 142 MSD LIB#: 2147 CN: 4-pentenoic acid, 2-methyl-, ethyl ester Synonyms: none Source: Bedoukian Res. 100



41



69 O



80 60



O



40 20 40



127



97



53 60



80



142



100



120



140



RT: 5.53 AI: 921 KI: 926 Tricyclene CAS#: 508-32-7 MF: C10 H16 FW: 136 MSD LIB#: 913 CN: tricyclo(2.2.1.02.6)heptane, 1,7,7-trimethylSynonyms: cyclone Source: Juniperus monticola f. compacta leaf oil, RP Adams #2580; 57.90% Cordia cylindrostachya, JEOR 2:209(1990); 6.76% Tsuga canadensis (conifer); 2.91% Anaphalis margaritacea 93



100 80 60 40 41 20 40



79 105



67



53 60



80



100



121 120



136 140



Appendix III: Mass Spectra



99



RT: 5.54 AI: 921 KI: 927 Methyl hexanoate CAS#: 106-70-7 MF: C7 H14 O2 FW: 130 MSD LIB#: 1099 CN: hexanoic acid, methyl ester Synonyms: methyl caproate Source: Aldrich Chem.; 6.04% Chaenomeles speciosa, JEOR 6:81(1994); 2.00% Magnolia grandiflora; 1.03% Michelia alba (flower absolute) 74



100



O



80



43



60



O



40



87



59



99



20 40



60



80



100



120



140



RT: 5.59 AI: 923 KI: 929 Pentenoic acid CAS#: 1575-74-2 MF: C6 H10 O2 FW: 114 MSD LIB#: 1968 CN: 4-pentenoic acid, 2-methylSynonyms: methyl-4-pentenoic acid, 2Source: Bedoukian Res. ex JJ Brophy 100



69



41



O



80 OH



60 40



99



55



20 40



60



80



114



100



120



RT: 5.61 AI: 923 KI: 929 Artemisia triene CAS#: 18383-70-5 MF: C10 H16 FW: 136 MSD LIB#: 213 CN: 1,3,6-heptatriene, 2,5,5-trimethyl-,(E)Synonyms: none Source: Artemisia perscia oil ex P. Weyerstahl; 1.40% Artemisia abaensis, p. 272, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.64% Artemisia occidentalis-sichaunensis; 0.15% Artemisia judaica 93



100 80



41



105



60



67



53



40



77



121 E



20



114 40



60



80



100



136 120



140



Adams: Essential Oil Components by GC/MS



100



RT: 5.62 AI: 924 KI: 930 Thujene CAS#: 2867-05-2 MF: C10 H16 FW: 136 MSD LIB#: 911 CN: bicyclo(3.1.0)hex-2-ene, 2-methyl-5-(1-methylethyl)Synonyms: origanene Source: Juniperus monticola f. compacta leaf oil, RP Adams #2580; 61.36% Boswellia serrata, FFJ 2:99(1987); 8.23% Ocimum gratissimum; 7.75% Cinnamomum burmannii 93



100 80 60



77



40 20 41



53



65



40



136



105



60



80



100



120



140



RT: 5.63 AI: 924 KI: 930 Cumene CAS#: 98-82-8 MF: C9 H12 FW: 120 MSD LIB#: 502 CN: benzene, (1-methylethyl)Synonyms: cumol; 2-phenylpropane; isopropylbenzene Source: Hopkins-Williams, UK ex Keith Harkiss; 0.72% Thuja occidentalis, J. Wood Chem. Technol. 8:561(1988); 0.01% Apium graveolens 105



100 80 60 40 20



120



77



51



91



40



60



80



100



120



140



RT: 5.66 AI: 925 KI: 931 Heptanone CAS#: 6137-11-7 MF: C8 H16 O FW: 128 MSD LIB#: 2012 CN: 3-heptanone, 4-methylSynonyms: none Source: Aldrich Chem. ex JJ Brophy 57



100



O



80



71



43



60 86



40 20



99 40



60



80



100



128 120



140



Appendix III: Mass Spectra



101



RT: 5.71 AI: 927 KI: 933 Hepten-2-one CAS#: 5609-09-6 MF: C7 H12 O FW: 112 MSD LIB#: 2019 CN: 3-hepten-2-one, (3E)Synonyms: trans-3-hepten-2-one Source: Bedoukian Res. ex JJ Brophy 55



100



O



80



E



60



43



97



40 20



112



69 40



60



80



100



120



RT: 5.71 AI: 927 KI: 933 Pentanoic acid CAS#: 97-61-0 MF: C6 H12 O2 FW: 116 MSD LIB#: 1971 CN: pentanoic acid, 2-methylSynonyms: Valeric acid, 2-methyl Source: Bedoukian Res. ex JJ Brophy 74



100



OH



80 O



60 40



43



20



87



55 40



60



80



100



120



140



RT: 5.72 AI: 927 KI: 934 Methyl-(3E)-hexenoate CAS#: 13894-61-6 MF: C7 H12 O2 FW: 128 MSD LIB#: 2046 CN: 3-hexenoic acid, methyl ester, (3E)Synonyms: none Source: Bedoukian Res. 100



41 E



80



OMe



68 74



60



O



59



40



128



20



87 40



60



80



97 100



113 120



140



Adams: Essential Oil Components by GC/MS



102



RT: 5.75 AI: 928 KI: 935 Thiazole CAS#: 3581-91-7 MF: C5 H7 N S FW: 113 MSD LIB#: 63 CN: thiazole, 4,5-dimethylSynonyms: none Source: Aldrich Chem. 113



71



100



N



80 S



60



45



40 53



20



85



59



98



40



60



80



100



120



RT: 5.78 AI: 929 KI: 936 Ethyl tiglate CAS#: 5837-78-5 MF: C7 H12 O2 FW: 128 MSD LIB#: 1960 CN: 2-butenoic acid, 2-methyl-, ethyl ester, (E)Synonyms: tiglic acid, ethyl ester; cortonic acid, 2-methyl-, ethyl ester, (E)Source: Bedoukian Res. ex JJ Brophy; 0.08% Gardenia jasminoides, p. 90, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.01% Spondias cytherea 55



100



83



80



E



O



60 O



40



113



100



20



128



43 40



60



80



100



120



140



RT: 5.80 AI: 930 KI: 937 Citronellene CAS#: 2051-30-1 MF: C10 H22 FW: 142 MSD LIB#: 454 CN: octane, 2,6-dimethylSynonyms: none Source: Fluka Chem. 57



100 80



43 71



60 40 20



113



85 40



60



80



100



142 120



140



Appendix III: Mass Spectra



103



RT: 5.80 AI: 930 KI: 937 Oxazole CAS#: 53833-30-0 MF: C7 H11 N O FW: 125 MSD LIB#: 1229 CN: 2-ethyl-4,5-dimethyl oxazole Synonyms: none Source: Bedoukian Res. ex Art Tucker 43



100



110



125



80



O



60



55



82



40



N



70



20 40



60



80



100



120



140



RT: 5.81 AI: 930 KI: 937 Ethyl 2-methyl pentanoate CAS#: 39255-32-8 MF: C8 H16 O2 FW: 144 MSD LIB#: 2148 CN: pentanoic acid, 2-methyl-, ethyl ester Synonyms: ethyl 2-methylvalerate Source: Bedoukian Res. 100



43



102 O



80 O



60



74



40



55



20



115



87 40



60



80



129 100



120



140



RT: 5.82 AI: 931 KI: 938 Allyl isovalerate CAS#: 2835-39-4 MF: C8 H14 O2 FW: 142 MSD LIB#: 112 CN: butanoic acid, 3-methyl-, 2-propenyl ester Synonyms: allyl 3-methylbutanoate; 2-propenyl 3-methylbutanoate Source: Aldrich Chem. 100



41 57



O



80



85



60



O



40 20



100 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



104



RT: 5.83 AI: 931 KI: 938 Cyclopentene CAS#: 864685-63-3 MF: C10 H14 FW: 134 MSD LIB#: 2091 CN: cyclopentene Synonyms: none Source: Lavandula luisieri oil ex Nicolas Baldovini 119



100 80 60



91



40



134



20 41



51



40



77



65 60



103 80



100



120



140



RT: 5.85 AI: 932 KI: 939 Norbornen-2-ol CAS#: 106928-44-3 MF: C7 H10 O FW: 110 MSD LIB#: 1178 CN: bicyclo(2.2.1)hept-5-en-2-ol, (1R-endo)Synonyms: none Source: ref. cpd. ex E. von Rudloff 66



100 80 60 40 20



41



110



40



60



80



100



120



RT: 5.85 AI: 932 KI: 939 Pinene CAS#: 80-56-8 MF: C10 H16 FW: 136 MSD LIB#: 912 CN: bicyclo(3.1.1)hept-3-ene, 2,6,6-trimethylSynonyms: 2-pinene Source: Juniperus lucayana leaf oil, RP Adams #2863; 88.13% Pinus kesiya, The Chemical Composition of Pinus kesiya oil from Yunnan, J-L Lo, in: Flav. & Frag.: A World Perspective, Lawrence, etal., (eds.), Proc. 10th Intl. Cong. Ess. Oils., Wash. DC(1996); 87.40% Sequoiadendron giganteum; 78.61% Pistacia lentiscus 93



100 80 60 40



77



41



20



53 40



105



67 60



80



100



121 120



136 140



Appendix III: Mass Spectra



105



RT: 5.89 AI: 933 KI: 940 Pentanoic acid CAS#: 646-07-1 MF: C6 H12 O2 FW: 116 MSD LIB#: 1986 CN: pentanoic acid, 4-methylSynonyms: valeric acid, 4-methyl-; isocaproic acid Source: Bedoukian Res. ex JJ Brophy 57



100



OH



80 60 40



O



73



41



20



83 40



60



80



100



120



140



RT: 5.95 AI: 935 KI: 943 Cyclohexanol CAS#: 591-23-1 MF: C7 H14 O FW: 114 MSD LIB#: 2011 CN: cyclohexanol, 3-methylSynonyms: none Source: Fluka Chem. ex JJ Brophy



OH



RT: 5.98 AI: 936 KI: 944 Heptanone CAS#: 541-85-5 MF: C8 H16 O FW: 128 MSD LIB#: 785 CN: heptanone, 5-methyl-3Synonyms: 3-methylbutyl ethyl ketone Source: Aldrich Chem. 43



100



57



80



O



71



60



99



40 20



128 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



106



RT: 6.00 AI: 937 KI: 944 Fruitaleur CAS#: 1617-23-8 MF: C8 H14 O2 FW: 142 CN: 3-pentenoic acid, 2-methyl-, ethyl ester Synonyms: ethyl 2-methyl-3-pentenoate Source: Bedoukian Res.



MSD LIB#: 2037



69



100



O



80



E O



60 41 40 20 40



142



127



53 60



80



100



120



140



RT: 6.05 AI: 939 KI: 946 Norbornen-2-ol CAS#: 71030-14-3 MF: C7 H10 O FW: 110 MSD LIB#: 1181 CN: bicyclo(2,2,1)hept-5-en-2-ol, (1S-exo)Synonyms: none Source: ref. cpd. ex E. von Rudloff 66



100 80 60 40 20



110



79 40



60



80



100



120



RT: 6.05 AI: 939 KI: 946 Valeric acid CAS#: 105-43-1 MF: C6 H12 O2 FW: 116 MSD LIB#: 1532 CN: pentanoic acid, 3-methylSynonyms: 3-methylpentanoic acid Source: acetoxyhexane, 2- ex JJ Brophy 60



100



O



80 60 40



OH



41



20



87



73 40



60



80



100



120



140



Appendix III: Mass Spectra



107



RT: 6.10 AI: 941 KI: 948 Acetoxyhexane CAS#: 5953-49-1 MF: C8 H16 O2 FW: 144 MSD LIB#: 2016 CN: 2-hexanol, acetate Synonyms: hex-2yl ethanoate Source: acetoxyhexane, 2- ex JJ Brophy 100



43 O-Ac



80 60 40



87



20



55 40



69 60



129 80



100



120



RT: 6.10 AI: 941 KI: 948 Valerolactone CAS#: 108-29-2 MF: C5 H8 O2 FW: 100 CN: 2(3H)-furanone, dihydro-5-methylSynonyms: γ-pentalactone Source: Aldrich Chem.



140



MSD LIB#: 1690



O



O



RT: 6.15 AI: 942 KI: 950 Citronellene CAS#: 2436-90-0 MF: C10 H18 FW: 138 CN: 1,6-octadiene, 3,7-dimethylSynonyms: dihydro myrcene Source: Fluka Chem. ex K. Harkiss 100



MSD LIB#: 453



41



80



55 67



60



82



40



95



20



123 40



60



80



100



120



138 140



Adams: Essential Oil Components by GC/MS



108



RT: 6.21 AI: 945 KI: 952 Cyclohexanone CAS#: 591-24-2 MF: C7 H12 O FW: 112 MSD LIB#: 532 CN: cyclohexanone, 3-methylSynonyms: none Source: ref. cpd. ex Art Tucker 69



100 80 60



O



41 56



40



112



20



97



79 40



60



80



100



120



RT: 6.21 AI: 945 KI: 952 Methyl pent-2-enolide (impure) CAS#: 20019-64-1 MF: C6 H8 O2 FW: 112 MSD LIB#: 194 CN: 2(5H)-furanone, 5,5-dimethylSynonyms: 4,4-dimethyl-2-butenolide Source: Armoise a davanone oil ex Guy Collin 43



100



97



69



O



80 60 40 53



20



112



82



40



60



80



100



120



RT: 6.22 AI: 945 KI: 952 Fenchene CAS#: 471-84-1 MF: C10 H16 FW: 136 MSD LIB#: 895 CN: bicyclo(2,2,1)heptane, 7,7-dimethyl-2-methyleneSynonyms: none Source: Juniperus angosturan leaf oil, RP Adams #2665; 4.10% Juniperus intermedia, FFJ 10:25(1995); 3.70% Artemisia velotiorum; 3.30% Juniperus communis 93



100 79



80 60 41 40



67



53



20 40



107



60



121 136



80



100



120



140



O



Appendix III: Mass Spectra



109



RT: 6.26 AI: 946 KI: 954 Camphene CAS#: 79-92-5 MF: C10 H16 FW: 136 MSD LIB#: 914 CN: 2,2-dimethyl-3-methylenebicyclo-(2.2.1)heptane Synonyms: none Source: Juniperus lucayana ex RP Adams #2863; common in conifers; 70.50% Eucalyptus kirtoniana, JEOR 7:215(1995); 32.08% Valeriana officinalis; 29.97% Abies sibirica 93



100 80 60 40



121



41



67



79 107



53



20 40



60



80



100



RT: 6.27 AI: 947 KI: 954 Heptenal CAS#: 18829-55-5 MF: C7 H12 O FW: 112 CN: 2-heptenal, (E)Synonyms: butylacrolein, 3-; heptanal, trans-2Source: Bedoukian Res. ex JJ Brophy 100



136 120



140



MSD LIB#: 1942



41 E



55



80



83



O



60 70



40 20



97 40



60



80



RT: 6.28 AI: 947 KI: 954 Heptenol CAS#: 1708-81-2 MF: C7 H14 O FW: 114 CN: 3-hepten-1-ol, (3Z)Synonyms: none Source: Bedoukian Res.



112



100



120



MSD LIB#: 2076



HO



Z



Adams: Essential Oil Components by GC/MS



110



RT: 6.34 AI: 949 KI: 956 Ethyl 3-methyl pentanoate CAS#: 5870-68-8 MF: C8 H16 O2 FW: 144 MSD LIB#: 2191 CN: pentanoic acid, 3-methyl-, ethyl ester Synonyms: ethyl 3-methylvalerate Source: Bedoukian Res. 88



100 80



41



O



60



O



60



40



99 71 115



20



129 40



60



80



100



120



RT: 6.35 AI: 950 KI: 957 Glycerol CAS#: 56-81-5 MF: C3 H8 O3 FW: 92 CN: 1,2,3-propanetriol Synonyms: glycerin, glycyl alcohol Source: Sigma Chem. 100



43



144 140



MSD LIB#: 1904



61 HO



80



OH OH



60 40 20



73 60



80



100



120



140



RT: 6.35 AI: 950 KI: 957 Mercaptopropanoic acid CAS#: 79-42-5 MF: C3 H6 O2 S FW: 106 MSD LIB#: 1651 CN: 2-mercaptopropanoic acid Synonyms: thiolactic acid, propionic acid Source: Aldrich Chem. 61



100



O



45



80 60



HS



40



106



20 40



60



80



100



120



OH



Appendix III: Mass Spectra



111



RT: 6.38 AI: 951 KI: 958 Thiazole CAS#: 15679-19-3 MF: C5 H7 N O S FW: 129 MSD LIB#: 55 CN: thiazole, 2-ethoxySynonyms: none Source: Aldrich Chem. 101



73



100 80 60



46



129



40



56



20



86 40



60



80



100



120



140



RT: 6.43 AI: 952 KI: 960 Benzaldehyde CAS#: 100-52-7 MF: C7 H6 O FW: 106 MSD LIB#: 310 CN: benzaldehyde Synonyms: artificial blackberry; artificial almond Source: artificial blackberry flavor, Lorann Inc.; 95.00% Prunus dulcis, p. 61, in: Die natuerlichen und kuenstilchen Aromen, Dr. Alfred Verlag Publ., Heidelberg(1982); 95.00% Prunus armeniaca (kernel); 10.07% Dendrobium chrysatoxum (flower) 77



100



106



H



80 51



60 40 20 40



60



80



100



120



RT: 6.44 AI: 953 KI: 960 Thuja-2,4(10)-diene CAS#: 36262-09-6 MF: C10 H14 FW: 134 MSD LIB#: 361 CN: bicyclo(3.1.0)hex-2-ene, 4-methylene-1-(1-methylethyl)Synonyms: none Source: carrot seed oil ex Nestle ex A Chainteau; 0.40% Pinus sibirica, JEOR 8:549(1996); 0.30% Juniperus rigida (Korea); 0.05% Juniperus rigida (Japan) 91



100 80 60 40 41 20 40



65



51 60



78 80



105 100



119 134 120



140



O



Adams: Essential Oil Components by GC/MS



112



RT: 6.49 AI: 954 KI: 962 Cyclohexyl formate CAS#: 4351-54-6 MF: C7 H12 O2 FW: 128 CN: formic acid, cyclohexyl ester Synonyms: cyclohexanol formate Source: Bedoukian Res. ex Art Tucker 67



100 80 60



MSD LIB#: 533



O



82 41



O



57



40 20 40



60



80



100



120



140



RT: 6.56 AI: 957 KI: 964 Furfural CAS#: 620-02-0 MF: C6 H6 O2 FW: 110 MSD LIB#: 1460 CN: 2-furancarboxaldehyde, 5-methylSynonyms: 5-methyl-2-furfuraldehyde Source: distilled comm. tamarind (Laxmi Brand, India) RP Adams #6440 100



H



110



53



O



80



O



60 40 43



20



81



40



60



80



100



120



RT: 6.58 AI: 958 KI: 965 Heptan-2-ol CAS#: 4730-22-7 MF: C8 H18 O FW: 130 MSD LIB#: 778 CN: 2-heptanol, 6-methylSynonyms: none Source: ref. cpd. ex P. Weyerstahl 45



100



OH



80 60 40



55



20



69 40



60



84 80



97 100



120



140



Appendix III: Mass Spectra



113



RT: 6.58 AI: 958 KI: 965 Hepten-1-ol CAS#: 33467-76-4 MF: C7 H14 O FW: 114 MSD LIB#: 1935 CN: 2-hepten-1-ol, (E)Synonyms: none Source: Bedoukian Chem. ex JJ Brophy E OH



RT: 6.59 AI: 958 KI: 965 Octen-5-yne CAS#: 850309-57-8 MF: C9 H14 FW: 122 MSD LIB#: 1909 CN: 3-octen-5-yne, 2-methyl-,(3E)Synonyms: none Source: Lomatium dissectum root oil ex Vasu Dev 100



91



79



80



E



122



60 40 41 20



107 65



51



40



60



80



100



RT: 6.63 AI: 959 KI: 966 Heptanol CAS#: 111-70-6 MF: C7 H16 O FW: 116 CN: 1-heptanol Synonyms: gentanol, enanthic alcohol Source: alcohols mix ex E. von Rudloff 100



41



120



140



MSD LIB#: 33



70



56



80 60 40 20



83 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



114



RT: 6.63 AI: 959 KI: 966 Hepten-1-ol CAS#: 6191-71-5 MF: C7 H14 O FW: 114 MSD LIB#: 787 CN: 4-hepten-1-ol, (Z)Synonyms: cis-hept-4-enol Source: Bedoukian Res. ex Art Tucker OH



Z



RT: 6.64 AI: 960 KI: 966 Isoamyl propionate CAS#: 105-68-0 MF: C8 H16 O2 FW: 144 CN: propionic acid, isopentyl ester Synonyms: isoamyl propionate, isopentyl propanoate Source: Aldrich Chem.



MSD LIB#: 1606



57



100



O



80 60



70



O



43



40 20



101 40



60



80



100



120



140



RT: 6.67 AI: 961 KI: 967 Verbenene CAS#: 4080-46-0 MF: C10 H14 FW: 134 MSD LIB#: 906 CN: bicyclo(3.1.1)hept-2-ene, 6,6-dimethyl-4-methyleneSynonyms: 2(10),3-pinadiene Source: Juniperus flaccida var. martinezii leaf oil, RP Adams #5974; Identified by R. Larent, Robertet, France 91



100 80



119



60 77



40 41 51



20 40



134



105



65 60



80



100



120



140



Appendix III: Mass Spectra



115



RT: 6.84 AI: 967 KI: 973 Hexanoic acid CAS#: 142-62-1 MF: C6 H12 O2 FW: 116 MSD LIB#: 2067 CN: hexanoic acid Synonyms: caproic acid Source: Bedoukian Res.; 6.17% Zizyphus jujuba fruit, JEOR 8:323(1996); 3.35% Passiflora edulis fruit; 2.70% Psidium guajava fruit 60



100



O



80



OH



60 73



40 20



41 87 40



60



80



100



120



140



RT: 6.85 AI: 967 KI: 973 Pyrazine CAS#: 2847-30-5 MF: C6 H8 N2 O FW: 124 MSD LIB#: 66 CN: pyrazine, 2-methoxy-3-methylSynonyms: none Source: Aldrich Chem. 124



100



N



O-Me



80 60



42



106



68 81



40



N



95



54



20 40



60



80



100



RT: 6.90 AI: 969 KI: 975 Methyl 2-furoate CAS#: 611-13-2 MF: C6 H6 O3 FW: 126 CN: 2-furancarboxylic acid, methyl ester Synonyms: pyromucic acid methyl ester; furoic acid, 2Source: Bedoukian Res.



120



140



MSD LIB#: 2066



95



100



O



80



O OMe



60 40



126



20 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



116



RT: 6.90 AI: 969 KI: 975 Propanol CAS#: 505-10-2 MF: C4 H10 OS FW: 106 MSD LIB#: 1708 CN: 1-propanol, 3-(methylthio)Synonyms: methionol Source: Aldrich Chem. 45



100 80



61



HO



106



60 73



40 20



88 40



60



80



100



RT: 6.91 AI: 969 KI: 975 Pinane CAS#: 33626-25-4 MF: C10 H18 FW: 138 CN: bicyclo(3.1.1)heptane, 2,6,6-trimethyl-,(1α,2α,5α)Synonyms: none Source: SCM Chems. ex H. Hills 100 41



55



120



MSD LIB#: 1296



95



80



67 81



60 40



109



20



123 138



40



60



80



100



120



140



RT: 6.91 AI: 969 KI: 975 Sabinene CAS#: 3387-41-5 MF: C10 H16 FW: 136 MSD LIB#: 304 CN: bicyclo(3.1.0)hexane, 4-methylene-1-(1-methylethyl)Synonyms: 4(10)-thujene Source: distillation of black pepper, RP Adams #5448; 82.90% Juniperus sabina, J. Chromatog. 396:416(1987); 62.36% Litsea cubeba (flower); 61.91% Citrus paradisi 93



100 80 60



77



40 41 20



53 40



69 60



121 80



100



120



136 140



S



Appendix III: Mass Spectra



117



RT: 6.93 AI: 970 KI: 976 Isopropyl tiglate CAS#: 1733-25-1 MF: C8 H14 O2 FW: 142 MSD LIB#: 42 CN: 2-butenoic acid, 2-methyl-, 1-methylethyl ester (E)Synonyms: tiglic acid isopropyl ester Source: Aldrich Chem. 83



100 80



55



O



43 O



60 40



127



101



20



142 40



60



80



100



120



140



RT: 6.93 AI: 970 KI: 976 Norborneol CAS#: 497-37-0 MF: C7 H12 O FW: 112 MSD LIB#: 1187 CN: bicyclo(2.2.1)heptan-2-ol, exoSynonyms: none Source: ref. cpd. ex E. von Rudloff OH



RT: 6.96 AI: 971 KI: 976 Artemiseole CAS#: 60485-46-3 MF: C10 H16 O FW: 152 MSD LIB#: 222 CN: 3-oxabicylo(3.1.0)hexane, 6-ethenyl-1,4,4-trimethyl-,(1R-(1α,5α,6α))Synonyms: arthole Source: Artemisia tridentata, SLC, UT ex RP Adams #5577 100



43 79



80



95



67



60 40



137



55 109



20 40



60



80



100



123 120



152 140



160



Adams: Essential Oil Components by GC/MS



118



RT: 6.98 AI: 972 KI: 977 Octen-3-one CAS#: 4312-99-6 MF: C8 H14 O FW: 126 CN: 1-octen-3-one Synonyms: amyl vinyl ketone; pentyl vinyl ketone Source: Bedoukian Res. 55



100



MSD LIB#: 2058



70



80 60



O



40



43



20



83 40



60



97



80



100



RT: 7.00 AI: 972 KI: 978 Octen-2-ol CAS#: 69668-89-9 MF: C8 H16 O FW: 128 CN: 3-octen-2-ol, (3Z)Synonyms: cis-3-octen-2-ol Source: Bedoukian Res. ex JJ Brophy



120



140



MSD LIB#: 2021



71



100



OH



Z



80 43



60



57



40 20



85 40



60



95



80



128 100



120



140



RT: 7.01 AI: 973 KI: 978 Hexanal, dimethyl acetal CAS#: 1599-47-9 MF: C8 H18 O2 FW: 146 MSD LIB#: 2112 CN: hexane, 1,1-dimethoxySynonyms: caproaldehyde dimethyl acetal Source: Bedoukian Res. 75



100



OMe



80 60



MeO



40 45



20 40



55



115



83 60



80



100



120



140



Appendix III: Mass Spectra



119



RT: 7.02 AI: 973 KI: 978 Dimethyl-4-heptanone CAS#: 19549-84-9 MF: C9 H18 O FW: 142 MSD LIB#: 1997 CN: 4-heptanone, 3,5-dimethylSynonyms: di-sec-butyl ketone Source: Aldrich Chem. ex JJ Brophy 57



100 80 60



O



40 20



85



41



142 40



60



80



100



120



140



RT: 7.03 AI: 973 KI: 979 Menthane CAS#: 1678-82-6 MF: C10 H20 FW: 140 MSD LIB#: 1075 CN: cyclohexane, 1-methyl-4-(1-methylethyl)-,transSynonyms: none Source: ref. cpd. ex E. von Rudloff 55



100 80



97



60 40 41



81



69



20 40



140



60



80



100



120



140



RT: 7.04 AI: 974 KI: 979 Octen-3-ol CAS#: 3391-86-4 MF: C8 H16 O FW: 128 MSD LIB#: 897 CN: octen-3-ol Synonyms: none Source: Juniperus bermudiana leaf oil, RP Adams #2554 57



100 80



OH



60 40



43



20



72 40



60



85 80



100



120



140



Adams: Essential Oil Components by GC/MS



120



RT: 7.04 AI: 974 KI: 979 Pinene CAS#: 127-91-3 MF: C10 H16 FW: 136 MSD LIB#: 305 CN: bicyclo(3.1.1)heptane, 6,6-dimethyl-2-methyleneSynonyms: nopinene; terebenthene; pseudopinene Source: distillation of black pepper, RP Adams #5448; 59.90% Ferula galbaniflua, J. Food Sci. 27:455(1962); 58.52% Amomum villosum; 55.10% Myristica fragrans 93



100 80 60



41



40



69



20



79



53



107



40



60



80



100



121



136



120



140



RT: 7.18 AI: 979 KI: 983 Mentha-2,8-diene CAS#: 5208-52-6 MF: C10 H16 FW: 136 MSD LIB#: 1067 CN: m-mentha-4,8-dien, (1R,3S)Synonyms: none Source: ref. cpd. ex K. Gollnick 79



100 80 60



93 41



40 20 40



107



67



55



60



80



100



121



136



120



140



RT: 7.19 AI: 979 KI: 983 Octanone CAS#: 106-68-3 MF: C8 H16 O FW: 128 MSD LIB#: 987 CN: 3-octanone Synonyms: ethyl pentyl ketone; amyl ethyl ketone Source: Lavender oil ex Firmenich ex AF Thomas; 6.15% Rosmarinus officinalis, JEOR 7:279(1995); 2.40% Elsholtzia ciliata; 2.27% Lavendula angustifolia 43



100 80



57



60



O



72



40



99



20



85 40



60



80



128 100



120



140



Appendix III: Mass Spectra



121



RT: 7.22 AI: 980 KI: 984 Isolimonene CAS#: 5113-87-1 MF: C10 H16 FW: 136 MSD LIB#: 867 CN: cyclohexene, 3-methyl-6-(1-methylethenyl)-, (3R-trans)Synonyms: none Source: Fluka Chem. 79



100 80 60



93 41



40



107



67



53



121



136



20 40



60



80



100



120



140



RT: 7.25 AI: 981 KI: 985 Hepten-2-one CAS#: 110-93-0 MF: C8 H14 O FW: 126 MSD LIB#: 789 CN: methyl-5-hepten-2-one (6-) Synonyms: 2-methyl-6-oxo-2-heptene Source: ref. cpd. ex Theresa Chamblee, Coca Cola Co. 43



100 80 60 40



55



69



20



108 93



83 40



60



80



126 100



120



140



RT: 7.26 AI: 982 KI: 985 Norborneol CAS#: 497-36-9 MF: C7 H12 O FW: 112 MSD LIB#: 1188 CN: bicyclo(2.2.1)heptan-2-ol, endoSynonyms: none Source: ref. cpd. ex E. von Rudloff 79



100 80 60



OH



67 94



41



40



55



20 40



60



80



100



120



Adams: Essential Oil Components by GC/MS



122



RT: 7.27 AI: 982 KI: 986 Pinane CAS#: 6876-13-7 MF: C10 H18 FW: 138 MSD LIB#: 1297 CN: bicyclo(3.1.1)heptane, 2,6,6-trimethyl-, (1α,2β,5α)Synonyms: none Source: SCM Chems. ex H. Hills 100



41



55 95



67



80



81



60 40



123



20



109 40



60



80



138



100



RT: 7.28 AI: 982 KI: 986 Octen-2-ol CAS#: 57648-55-2 MF: C8 H16 O FW: 128 CN: 3-octen-2-ol, (3E)Synonyms: trans-3-octen-2-ol Source: Bedoukian Res. ex JJ Brophy



120



140



MSD LIB#: 2020



71



100



OH



80 E



43



60



57



40 20



85 40



60



95



80



128 100



120



140



RT: 7.30 AI: 983 KI: 987 Hexenoic acid CAS#: 1577-18-0 MF: C6 H10 O2 FW: 114 MSD LIB#: 1976 CN: 3-hexenoic acid, (E)Synonyms: trans-3-hexenoic acid Source: Bedoukian Res. ex JJ Brophy 100



41



55



E



O



80 60



OH



114



68



40 20



99 40



60



80



100



120



Appendix III: Mass Spectra



123



RT: 7.31 AI: 983 KI: 987 Mentha-2,8-diene CAS#: 5208-51-5 MF: C10 H16 FW: 136 MSD LIB#: 1068 CN: m-mentha-4,8-diene, (1S,3S)Synonyms: none Source: ref. cpd. ex K. Gollnick 79



100



93



80 60 40



41 53



20 40



121



107



67



60



80



136



100



120



140



RT: 7.31 AI: 983 KI: 987 Methyl pentanoate CAS#: 40348-72-9 MF: C7 H14 O3 FW: 146 MSD LIB#: 1107 CN: pentanoic acid, 2-hydroxy-4-methyl, methyl ester Synonyms: none Source: ref. cpd. ex KC Wong, Malaysia 100



69



43



OH



80



Me-O



60



87 O



40 20



57 127 40



60



80



100



120



140



RT: 7.32 AI: 984 KI: 987 Menthene CAS#: 500-00-5 MF: C10 H18 FW: 138 MSD LIB#: 1077 CN: cyclohexene, 4-methyl-1-(1-methylethyl)Synonyms: menthomenthene; isopropyl-4-methylcyclohexene Source: ref. cpd. ex E. von Rudloff 100



81



95



80 67



60 41 40



55 123



20



138



109 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



124



RT: 7.34 AI: 984 KI: 988 Pentyl furan CAS#: 3777-69-3 MF: C9 H14 O FW: 138 MSD LIB#: 1961 CN: furan, 2-pentylSynonyms: 2-amylfuran Source: Bedoukian Res. ex JJ Brophy; 1.00% Spartium junceum, Rivista Ital. EPPOS 325(1992); 0.60% Apium graveolens; 0.25% Rhus coriaria 81



100 80 60 40 20



41



53



40



138



95 60



80



100



120



O



140



RT: 7.39 AI: 986 KI: 989 Decene CAS#: 872-05-9 MF: C10 H20 FW: 140 MSD LIB#: 1219 CN: decene (1-) Synonyms: none Source: Olefins stock mix, Aldrich and Sigma Chem.; 6.20% Nicotiana rustica, JEOR 7:265(1995); 0.30% Machilus bombycina; 0.20% Minthostachys spicata 100



41



80



55



60



70



40



83



20 40



60



80



97 100



RT: 7.42 AI: 987 KI: 990 Furfuryl acetate CAS#: 623-17-6 MF: C7 H8 O3 FW: 140 CN: 2-furanmethanol, acetate Synonyms: acetic acid furfuryl ester; NSC 5585 Source: Bedoukian Res.



140 120



140



MSD LIB#: 2039



81



100



O



80 60



111



OAc



43



98 52



140



40 20



69 40



60



80



100



120



140



Appendix III: Mass Spectra



125



RT: 7.43 AI: 988 KI: 990 Myrcene CAS#: 123-35-3 MF: C10 H16 FW: 136 MSD LIB#: 915 CN: 1,6-octadiene, 7-methyl-3-methyleneSynonyms: none Source: Juniperus lucayana leaf oil, RP Adams #2863; 94.51% Alpinia galanga (root), JEOR 4:81(1992); 72.25% Pistacia lentiscus (ripe fruit); 68.00% Canella winterana (leaf) 100



41



80



93 69



60 40 20



79



53



136



40



60



80



100



120



140



RT: 7.44 AI: 988 KI: 991 Octanol CAS#: 589-98-0 MF: C8 H18 O FW: 130 MSD LIB#: 1257 CN: octan-3-ol Synonyms: none Source: Peppermint oil, McCormick Co.; 10.30% Mentha x gentilis, Phytochem. 11:2639(1972); 3.95% Perilla frutescens; 3.60% Teucrium heterophyllum 59



100 80 60 40



83



41



101



20



129 40



60



80



100



120



140



RT: 7.45 AI: 988 KI: 991 Cineole CAS#: 66113-06-2 MF: C10 H16 O FW: 152 MSD LIB#: 227 CN: 2-oxabicyclo(2.2.2)oct-5-ene, 1,3,3-trimethylSynonyms: none Source: Artemisia tridentata, RP Adams #5577, SLC, Utah; 5.20% Artemisia campestris, FFJ 10:25(1995); 1.10% Artemisia velotiorum; 0.70% Artemisia persica 109



100 80



O



60 40



79



43



94



20 40



124



67



49 60



131 137 80



100



120



140



152 160



Adams: Essential Oil Components by GC/MS



126



RT: 7.45 AI: 988 KI: 991 Octanone CAS#: 111-13-7 MF: C8 H16 O FW: 128 MSD LIB#: 1205 CN: 2-octanone Synonyms: methyl hexyl ketone Source: Chemical Services inc. ex H. Hills; 0.40% Ruta graveolens, Sci. Pharm 56:121(1988); 0.17% Zizyphus jujuba; 0.10% Dracocephalum kotschyi 43



100 80



58



60 40 20



71 40



128



60



80



100



120



140



RT: 7.47 AI: 989 KI: 991 Hepten-2-ol CAS#: 1569-60-4 MF: C8 H16 O FW: 128 MSD LIB#: 788 CN: 5-hepten-2-ol, 6-methylSynonyms: none Source: ref. cpd. ex E. von Rudloff 100



41



95 OH



80 60



69



55



40 20



110



81 40



60



80



100



128 120



140



RT: 7.48 AI: 989 KI: 992 Heptanol CAS#: 13254-34-7 MF: C9 H20 O FW: 144 MSD LIB#: 781 CN: 2-heptanol, 2,6-dimethylSynonyms: freesiol Source: H & R Chem. ex Art Tucker 59



100 80 60 40 20



69



43



129 40



60



80



100



120



140



Appendix III: Mass Spectra



127



RT: 7.48 AI: 989 KI: 992 Methyl pentanoate CAS#: 41654-19-7 MF: C7 H14 O3 FW: 146 MSD LIB#: 1108 CN: pentanoic acid, 2-hydroxy-3-methyl-, methyl ester Synonyms: none Source: ref. cpd. ex KC Wong, Malaysia 45



100



90



OH



80



O



60 40



O



57



69



20



75 40



60



80



100



120



140



RT: 7.52 AI: 991 KI: 993 Linalool oxide CAS#: 54750-70-8 MF: C10 H16 O FW: 152 MSD LIB#: 1011 CN: furan, 2-ethenyltetrahydro-2-methyl-5-(1-methylethenyl)-, transSynonyms: none Source: Bedoukian Res. ex Art Tucker 67



100 80



43 55



60



O



40



H



82



20 40



60



96



80



110



100



120



RT: 7.58 AI: 993 KI: 994 Butyl butanoate CAS#: 109-21-7 MF: C8 H16 O2 FW: 144 CN: butanoic acid, butyl ester Synonyms: butyl butyrate Source: Aldrich Chem. 100



137



152



140



160



MSD LIB#: 323



71 O



43



80 56



60



O



89



40 20 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



128



RT: 7.60 AI: 994 KI: 995 Octanol CAS#: 123-96-6 MF: C8 H18 O FW: 130 MSD LIB#: 32 CN: 2-octanol Synonyms: capryl alcohol Source: ref. cpd. ex E. von Rudloff; 0.01% Thymus vulgare, Bioflavour 87:327(1988) 45



100



OH



80 60 40 55



20



97 40



60



80



100



RT: 7.61 AI: 994 KI: 995 Mesitylene CAS#: 108-67-8 MF: C9 H12 FW: 120 CN: benzene, 1,3,5-trimethylSynonyms: trimethyl benzene Source: Artemisia judica oil ex Z. Fleisher



120



140



MSD LIB#: 202



105



100 80 60



120



40 20



41



51



65



40



77



60



91 80



100



120



140



RT: 7.62 AI: 994 KI: 995 Isobutyl-(2E)-butenoate CAS#: 589-66-2 MF: C8 H14 O2 FW: 142 MSD LIB#: 1611 CN: 2-butenoic acid, 2-methylpropyl ester Synonyms: isobutyl crotonate Source: Aldrich Chem. 69



100



E



80



O



60



20



O



87



40 43 40



56 127 60



80



100



120



140



Appendix III: Mass Spectra



129



RT: 7.62 AI: 994 KI: 995 Thiazole CAS#: 13623-11-5 MF: C6 H9 N S FW: 127 MSD LIB#: 70 CN: thiazole, 2,4,5-trimethylSynonyms: none Source: Aldrich Chem. 71



100



N



80



127



86



S



60 40



45



20



59



40



60



80



100



120



140



RT: 7.71 AI: 997 KI: 998 Ethyl hexanoate CAS#: 123-66-0 MF: C8 H16 O2 FW: 144 MSD LIB#: 79 CN: hexanoic acid, ethyl ester Synonyms: ethyl caproate Source: Aldrich Chem.; 61.01% Michelia balansae, p. 15, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 9.58% Michelia figo; 7.90% Pyrus serotina (Asian) 100 80



88 43



60



60



40



99 70



20



115 40



60



80



100



144 120



140



RT: 7.72 AI: 998 KI: 998 Octanal CAS#: 124-13-0 MF: C8 H16 O FW: 128 MSD LIB#: 37 CN: 1-octanal Synonyms: caprylaldehyde Source: ref. cpd. ex E. von Rudloff; 16.70% Carum carvi, FFJ 2:83(1987); 14.17% Citrus sinensis; 8.70% Zanthoxylum avicennae 100



41 O



80 57



60 40



84



69



20



100 40



60



80



100



110 120



140



Adams: Essential Oil Components by GC/MS



130



RT: 7.74 AI: 998 KI: 999 Furfuryl methyl sulfide CAS#: 1438-91-1 MF: C6 H8 O S FW: 128 MSD LIB#: 726 CN: furan, 2-((methylthio)methyl)Synonyms: none Source: Aldrich Chem. ex Art Tucker 81



100



O



80



S-Me



53



60 128



40 45



20 40



60



80



100



120



140



RT: 7.75 AI: 999 KI: 999 Yomogi alcohol CAS#: 26127-98-0 MF: C10 H18 O FW: 154 MSD LIB#: 231 CN: 3,6-heptadien-2-ol, 2,5,5-trimethyl-, (E)Synonyms: none Source: Artemisia vestita oil ex P. Weyerstahl; 4.70% Artemisia persica, JEOR 4:1(1992); 3.00% Artemisia judaica; 3.00% Artemisia annua 100



43



80



HO



E



60



59



40



85



67



20 40



60



97



80



139



121



100



120



140



160



RT: 7.77 AI: 1000 KI: 1000 Decane CAS#: 124-18-5 MF: C10 H22 FW: 142 MSD LIB#: 89 CN: decane Synonyms: none Source: Alkanes mix, Alltech Assoc.; 10.50% Acacia praecox (flower), FFJ 11:3(1996); 2.08% Cymbidium sinense (flower); 1.30% Narcissus tazetta 100



43 57



80 60 40



71



85



20



142



99 40



60



80



100



120



140



Appendix III: Mass Spectra



131



RT: 7.77 AI: 1000 KI: 1000 Pyrazine CAS#: 14667-55-1 MF: C7 H10 N2 FW: 122 MSD LIB#: 68 CN: pyrazine, trimethylSynonyms: none Source: Aldrich Chem. 100



42 N



80 60



122



N



40 20



81



54 40



60



80



100



120



140



RT: 7.79 AI: 1000 KI: 1000 Mentha-1(7),8-diene CAS#: 13837-95-1 MF: C10 H16 FW: 136 MSD LIB#: 1065 CN: cyclohexane, 1-methylene-3-(1-methylethenyl)Synonyms: none Source: ref. cpd. ex K. Gollnick 79



100 80 60



93



41 53



40



121



67



108



20



136 40



60



80



100



RT: 7.84 AI: 1001 KI: 1002 Carene CAS#: 554-61-0 MF: C10 H16 FW: 136 CN: bicyclo(4.1.0)hept-2-ene, 3,7,7-trimethylSynonyms: none Source: Aldrich Chem.



120



MSD LIB#: 355



93



100 80 60 40



140



121 77



41



136 53



20 40



105



65 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



132



RT: 7.84 AI: 1001 KI: 1002 Hexenyl acetate CAS#: 3681-82-1 MF: C8 H14 O2 FW: 142 MSD LIB#: 807 CN: 3-hexen-1-ol, acetate, (E)Synonyms: trans-3-hexenol acetate Source: acetylation of (E)-3-hexenol(6345); 0.55% Psidium guajava, FFJ 6:143(1991); 0.10% Anthriscus cerefolium; 0.02% Ruta graveolens 100



43 E



80



O-Ac



67



60 40



82



20



54 40



60



80



100



120



140



RT: 7.85 AI: 1002 KI: 1002 Phellandrene CAS#: 99-83-2 MF: C10 H16 FW: 136 MSD LIB#: 159 CN: methyl-5-(1-methylethyl)-1,3-cyclohexadiene Synonyms: menthadiene; p-mentha-1,5-diene; 1,3-cyclohexadiene Source: distillation of black pepper, RP Adams #5452; 58.00% Anethum graveolens (herb), JEOR 7:11(1995); 55.42% Schinus molle; 48.80% Monodora myristica 93



100 80 60 77



40 20 41 40



136



65



51 60



80



100



120



140



RT: 7.85 AI: 1002 KI: 1002 Pyrazine CAS#: 15707-23-0 MF: C7 H10 N2 FW: 122 MSD LIB#: 64 CN: pyrazine, 2-ethyl-3-methylSynonyms: none Source: Aldrich Chem. 121



100



N



80 60 40 20



N



42



40



67 52



80



94 107



60



80



100



120



140



Appendix III: Mass Spectra



133



RT: 7.89 AI: 1003 KI: 1004 Mentha-1(7),8-diene CAS#: 499-97-8 MF: C10 H16 FW: 136 MSD LIB#: 796 CN: cyclohexane, 1-methylene-4-(1-methylethenyl)Synonyms: pseudolimonene Source: Heteropyxis natalensis oil ex P. Weyerstahl 93



100 80 60 40



79



41 67



53



20 40



107 60



80



136



121



100



120



140



RT: 7.91 AI: 1003 KI: 1004 Ethyl-(3E)-hexenoate CAS#: 2396-83-0 MF: C8 H14 O2 FW: 142 MSD LIB#: 1943 CN: 3-hexenoic acid, ethyl ester-, (3E)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 100



41



69



E



O



80 O



60 40 55



20 40



88 60



80



142 97 100



127 120



140



RT: 7.93 AI: 1004 KI: 1005 Hexenyl acetate CAS#: 3681-71-8 MF: C8 H14 O2 FW: 142 MSD LIB#: 808 CN: 3-hexen-1-ol, acetate, (Z)Synonyms: cis-3-hexenyl acetate Source: acetylation of (Z)-3-hexenol(6345); 11.00% Psidium guajava, FFJ 6:143(1991); 8.12% Valeriana officinalis; 7.82% Convallaria majalis 100



43 Z



80 67



60 40



82



20



54 40



60



80



100



120



140



O-Ac



Adams: Essential Oil Components by GC/MS



134



RT: 7.96 AI: 1005 KI: 1006 Cresol methyl ether CAS#: 578-58-5 MF: C8 H10 O FW: 122 MSD LIB#: 1664 CN: benzene, 1-methoxy-2-methylSynonyms: o-methyltoluene, o-methylanisole Source: Aldrich Chem.; 0.44% Pistacia lentiscus, Chimika Chronika 10:119(1988); 0.17% Boswellia carterii 77



100



O-Me



107



80



122



60 40



91



51 63



20 40



60



80



100



120



140



RT: 7.99 AI: 1005 KI: 1007 Heptadienal CAS#: 4313-03-5 MF: C7 H10 O FW: 110 MSD LIB#: 2060 CN: 2,4-heptadienal, (2E,4E)Synonyms: trans, trans-2,4-heptadienal Source: Bedoukian Res.; 0.60% Melissa officinalis, Lebensm.-Wisc. U.-Technol. 19:482(1986); 0.10% Narcissus tazetta (absolute); 0.10% Rhus coriaria 81



100



E



80



E



60 40 20



41



53



40



110



67 60



80



100



120



RT: 7.99 AI: 1005 KI: 1007 Hexenoic acid CAS#: 13419-69-7 MF: C6 H10 O2 FW: 114 MSD LIB#: 2062 CN: 2-hexenoic acid, (2E-) Synonyms: none Source: Bedoukian Res.; 0.10% Gardenia jasminoides, JEOR 8:241(1996); 0.03% Spartium junceum; 0.01% Zizyphus jujuba fruit 73



100



O



80 60



E



42



40



OH



55 99



20



81 40



60



80



100



114 120



O



Appendix III: Mass Spectra



135



RT: 7.99 AI: 1005 KI: 1007 Pentyl propanoate CAS#: 624-54-4 MF: C8 H16 O2 FW: 144 CN: propanoic acid, pentyl ester Synonyms: amyl propionate; pentyl propionate Source: Pfaltz & Bauer ex Art Tucker



MSD LIB#: 1251



57



100



O



80 O



60 40



75



43



20



87 40



60



80



100



120



140



RT: 8.01 AI: 1006 KI: 1008 Linalool oxide CAS#: 54750-69-5 MF: C10 H16 O FW: 152 MSD LIB#: 1012 CN: furan, 2-ethenyltetrahydro-2-methyl-5-(1-methylethenyl)-,cisSynonyms: none Source: Bedoukian Res. ex Art Tucker 67



100 80



55 43



O



60 40



H



82



20 40



60



96



80



110



100



137 120



RT: 8.03 AI: 1007 KI: 1008 Sylvestrene CAS#: 499-03-6 MF: C10 H16 FW: 136 CN: cyclohexene, 1-methyl-3-(1-methylethenyl)Synonyms: m-mentha-1,8-diene Source: ref. cpd. ex K. Gollnick



160



MSD LIB#: 1066



93



100 80



121



79



60 40



140



136



41 67



55



20 40



60



107 80



100



120



140



Adams: Essential Oil Components by GC/MS



136



RT: 8.05 AI: 1007 KI: 1009 Hexyl acetate CAS#: 142-92-7 MF: C8 H16 O2 FW: 144 MSD LIB#: 185 CN: acetic acid, hexyl ester Synonyms: none Source: distillation of red delicious apples, RP Adams #5756; 6.94% Mandragora officinarum, JEOR 4:187(1992); 5.00% Anthemis nobilis; 3.95% Rosa chinensis 100



43



80 60 56



40 20



69 40



84



60



80



100



120



140



RT: 8.05 AI: 1007 KI: 1009 Isoamyl isobutyrate CAS#: 2050-01-3 MF: C9 H18 O2 FW: 158 MSD LIB#: 1603 CN: propanoic acid, 2-methyl-, 3-methylbutyl ester Synonyms: isopentyl isobutyrate Source: Aldrich Chem.; 3.60% Eriocephalus punctualis, Aromatic Plants: Basic & Applied, N. Margaris, etal., eds., Martinus Nijhoff Publ., The Netherlands(1982); 2.22% Anthemis nobilis; 0.10% Pteronia incana 100



43



80



70



O



60



O



40



55 89



20



115 40



60



80



100



120



140



160



RT: 8.10 AI: 1008 KI: 1011 Carene CAS#: 13466-78-9 MF: C10 H16 FW: 136 MSD LIB#: 1655 CN: trimethylbicyclo(4.1.0)hept-3-ene Synonyms: none Source: Juniperus gamboana ex RP Adams #2574; common in conifers; black pepper; 65.30% Pistacia lenticus, FFJ 6:229(1991); 54.60% Robinia pseudoacacia; 44.00% Abies semenovii 93



100 80 60 40



77



41



20



53 40



105



65 60



80



100



121 120



136 140



Appendix III: Mass Spectra



137



RT: 8.17 AI: 1010 KI: 1013 Hexenyl acetate CAS#: 2497-18-9 MF: C8 H14 O2 FW: 142 MSD LIB#: 2048 CN: 2-hexen-1-ol, acetate, (2E)Synonyms: none Source: Bedoukian Res.; 1.80% Valeriana officinalis, Dragoco Rept. 3:31(1/1992); 0.29% Lawsonia inermis; 0.24% Spondias cytherea 100



43 E



80



Ac-O



60 40



67



20



82



55 40



60



100



80



142



100



120



140



RT: 8.18 AI: 1011 KI: 1013 Dichlorobenzene CAS#: 106-46-7 MF: C6 H4 Cl2 FW: 146 MSD LIB#: 590 CN: benzene, 1,4-dichloroSynonyms: p-dicholorobenzene; paracide; parazene; para crystals Source: ENOZ Inc., mothballs 146



100



Cl



80 60



111



75



50



40 20 40



Cl



85



61 60



80



100



120



140



RT: 8.22 AI: 1012 KI: 1014 Cineole CAS#: 470-67-7 MF: C10 H18 O FW: 154 MSD LIB#: 1001 CN: 7-oxabicyclo(2.2.1) heptane, 1-methyl-4-(1-methylethyl)Synonyms: p-menthane, 1,4-epoxySource: West Indian lime oil ex Lorann Co.; 1.70% Citrus aurantifolia, p. 325, in: Flav. & Frag : A World Persp., Lawrence, etal., Proc. 10th Intl. Cong. of Ess Oil, Elsevier, Amsterdam(1988); 1.06% Terminalia bentzoe; 0.80% Eucalyptus globulus 100



43



80



111



60



55



40



81



20 40



O



71



60



80



125 93



154 139



100



120



140



160



Adams: Essential Oil Components by GC/MS



138



RT: 8.24 AI: 1012 KI: 1015 Isopropyl-4-methyl thiazole CAS#: 15679-13-7 MF: C7 H11 N S FW: 141 MSD LIB#: 1624 CN: thiazole, 4-methyl-2-(1-methylethyl)Synonyms: thiazole Source: Aldrich Chem. 126



100 80 60



N



40



45



71



S



141



20



99 40



60



80



100



120



140



RT: 8.27 AI: 1013 KI: 1016 Heptadienol CAS#: 33467-79-7 MF: C7 H12 O FW: 112 MSD LIB#: 2103 CN: 2,4-heptadien-1-ol, (2E,4E)Synonyms: none Source: Bedoukian Res. 55



100 80



83



41



E



OH



60



68



40



112 94



20 40



60



80



100



120



RT: 8.30 AI: 1014 KI: 1017 Terpinene CAS#: 99-86-5 MF: C10 H16 FW: 136 MSD LIB#: 900 CN: 1,3-cyclohexadiene, 1-methyl-4-(1-methylethyl)Synonyms: p-mentha-1,3-diene; terpilene Source: Juniperus coahuilensis leaf oil, RP Adams #2121; 16.83% Coleus aromaticus, J. Ethnopharmacol. 32:57(1991); 11.90% Melaleuca alternifolia; 10.70% Citrus paradisi 121



93



100 80 60



136



77



40 43



20 40



E



51



105



65 60



80



100



120



140



Appendix III: Mass Spectra



139



RT: 8.32 AI: 1014 KI: 1018 Thiazole CAS#: 24295-03-2 MF: C5 H5 N O S FW: 127 MSD LIB#: 52 CN: ethanone, 1-(2-thiazolyl)Synonyms: ketone, methyl 2-thiazolyl Source: Aldrich Chem. 43



100



N



Ac



80 S



60 40



99



58



20



85 40



60



127



112



80



100



120



140



RT: 8.34 AI: 1015 KI: 1018 Anisole CAS#: 104-93-8 MF: C8 H10 O FW: 122 MSD LIB#: 172 CN: benzene, 1-methoxy-4-methylSynonyms: p-methoxytoluene; p-methylanisole; cresol, methyl ether Source: Aldrich Chem. 122



100



O-Me



80 77



60 40 51



20 40



107



91 65 60



80



100



120



140



RT: 8.41 AI: 1017 KI: 1020 Ethyl 2-methyl-2-pentenoate CAS#: 1617-40-9 MF: C8 H14 O2 FW: 142 MSD LIB#: 2144 CN: 2-pentenoic acid, 2-methyl-, ethyl ester, (2E-) Synonyms: none Source: Bedoukian Res. 100



41 O



69



80 O



60



97



40



40



142



113



53



20



127 60



80



100



120



140



E



Adams: Essential Oil Components by GC/MS



140



RT: 8.41 AI: 1017 KI: 1020 Pyrazine CAS#: 22047-25-2 MF: C6 H6 N2 O FW: 122 MSD LIB#: 50 CN: ethanone, 1-pyrazinylSynonyms: ketone, methyl pyrazinyl Source: Aldrich Chem. 43



100



Ac



N



80 60



52



N



80



40



122



94



20 40



60



80



100



120



140



RT: 8.43 AI: 1017 KI: 1021 Cyclopentanedione CAS#: 765-70-8 MF: C6 H8 O2 FW: 112 MSD LIB#: 1691 CN: 1,2-cyclopentanedione, 3-methylSynonyms: methyl cyclopentanone Source: Aldrich Chem.



80



O



55



100



69



41



O



112



83



60 40 20



97 40



60



80



100



120



RT: 8.51 AI: 1019 KI: 1023 Ethyl 2-methyl-2-pentenoate CAS#: 1617-39-6 MF: C8 H14 O2 FW: 142 MSD LIB#: 2145 CN: 2-pentenoic acid, 2-methyl-, ethyl ester, (2Z-) Synonyms: none Source: Bedoukian Res. 100



41 69



80



O



Z



60



O



97



40



53



20



142 113



85 40



60



80



127 100



120



140



Appendix III: Mass Spectra



141



RT: 8.53 AI: 1020 KI: 1024 Cymene CAS#: 99-87-6 MF: C10 H14 FW: 134 MSD LIB#: 306 CN: benzene, 1-methyl-4-(1-methylethyl)Synonyms: p-isopropyltoluene; p-cymol; camphogen Source: Black pepper distillation ex Shilling Co.; 83.75% Origanum saccatum, JEOR 7:175(1995); 53.07% Origanum solymicum; 44.13% Thymus vulgaris 119



100 80 60 40 20



91 41 40



77



65



51



134



60



103 80



100



RT: 8.57 AI: 1021 KI: 1025 Allyl tiglate CAS#: 7493-71-2 MF: C8 H12 O2 FW: 140 CN: 2-butenoic acid, 2-methyl-, 2-propenyl ester, (E)Synonyms: tiglic acid, allyl ester Source: Aldrich Chem. 55



100



120



140



MSD LIB#: 43



83



O



80 E



60 40 41 125



95



20



140 40



60



80



100



120



140



RT: 8.57 AI: 1021 KI: 1025 Methyl heptanoate CAS#: 106-73-0 MF: C8 H16 O2 FW: 144 MSD LIB#: 1098 CN: heptanoic acid, methyl ester Synonyms: methyl enanthate Source: Aldrich Chem.; 0.37% Humulus lupulus (Neomexicanus cultivar), Z. Naturforsch. 37a:565(1982) 74



100



O



80 60



43



40



O



87



55



20 40



101 60



80



100



113 120



140



O



Adams: Essential Oil Components by GC/MS



142



RT: 8.57 AI: 1021 KI: 1025 Trimethyl benzene CAS#: 95-63-6 MF: C9 H12 FW: 120 MSD LIB#: 203 CN: benzene, 1,2,4-trimethylSynonyms: pseudocumene; methyl-p-xylene; psi.-cumene Source: Artemisia judica oil ex Z Fleisher; 0.68% Artemisia judaica, JEOR 2:271(1990); 0.10% Lawsonia inermis; 0.01% Murraya koenigii 105



100 80 60



120



40 20



41



51



65



40



77



60



91 80



100



120



140



RT: 8.58 AI: 1021 KI: 1026 Menthene CAS#: 5502-88-5 MF: C10 H18 FW: 138 MSD LIB#: 1076 CN: cyclohexene, 1-methyl-4-(1-methylethyl)Synonyms: carvomenthene; 4-isopropyl-1-methylcyclohexene Source: ref. cpd. ex E. von Rudloff 95



100 67



80 60 41 40



81



55



123



20 40



60



80



100



138



120



140



RT: 8.59 AI: 1022 KI: 1026 Cymene CAS#: 527-84-4 MF: C10 H14 FW: 134 MSD LIB#: 1529 CN: benzene, 1-methyl-2-(1-methylethyl)Synonyms: none Source: Valencia orange leaf oil ex MG Moshonas, USDA; 2.20% Achillea colina, Rastit. Resur 21:69(1985); 0.50% Boswellia carterii; 0.46% Persea podadenia (leaf) 119



100 80 60 40 20



91 41 40



65



51 60



77



134 103



80



100



120



140



Appendix III: Mass Spectra



143



RT: 8.69 AI: 1024 KI: 1029 Limonene CAS#: 138-86-3 MF: C10 H16 FW: 136 MSD LIB#: 164 CN: methyl-4-(1-methylethenyl)cyclohexene Synonyms: cajeputene; cinene; kautschin; nesol; p-mentha-1,8-diene; dipentene Source: distillation of sweet anis leaves. Calif., RP Adams #5452; 96.49% Citrus sinensis, Zhiwu, Xuebao, 30:623(1988); 96.41% Citrus aurantium; 95.00% Citrus deliciosa 68



100 80



93



60 40 41



79



53



107



20 40



60



80



100



121 120



136 140



RT: 8.70 AI: 1025 KI: 1029 Phellandrene CAS#: 555-10-2 MF: C10 H16 FW: 136 MSD LIB#: 161 CN: methyl-6-(1-methylethyl)cyclohexene Synonyms: p-menth-1(7),2-diene Source: distillation of sweet anis leaves(Calif.), RP Adams #5452; 63.05% Levisticum officinale, p. 641, in: Flav. & Frag.: A World Persp., Lawrence, etal., Elsevier Science Publishers, Amsterdam(1988); 61.00% Angelica archangelica; 21.00% Lavandula pinnata 93



100 80 60 77



40 20



41



136 65



53



40



60



121 80



100



RT: 8.73 AI: 1025 KI: 1030 Sylvestrene CAS#: 1461-27-4 MF: C10 H16 FW: 136 CN: cyclohexene, 1-methyl-5-(1-methylethenyl)Synonyms: m-mentha-1(6),8-diene Source: ref. cpd. ex E. von Rudloff



120



140



MSD LIB#: 1453



93



100 80 68



60 40 41 20 40



79 53



107 60



80



100



121 120



136 140



Adams: Essential Oil Components by GC/MS



144



RT: 8.76 AI: 1026 KI: 1031 Cineole CAS#: 470-82-6 MF: C10 H18 O FW: 154 MSD LIB#: 160 CN: 2-oxabicylco(2.2.2)octane, 1,3,3-trimethylSynonyms: cajeputol, 1,8-epoxy-p-menthane; eucalyptol; zedoary oil; eucapur; trepan Source: Foeniculum vulgare(Calif. anis) leaf oil; 95.13% Eucalyptus globulus, p. 52, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 70.00% Melaleuca viridiflora; 69.00% Eucalyptus cinerea 100



43



80 O



60 40



71



55



81



108



93



139



20



154



125 40



60



80



100



120



140



160



RT: 8.77 AI: 1026 KI: 1031 Benzyl alcohol CAS#: 100-51-6 MF: C7 H8 O FW: 108 MSD LIB#: 288 CN: benzenemethanol Synonyms: phenylmethanol; benzenecarbinol; α-hydroxytoluene Source: Jasmin absolute ex A.F.Thomas; 35.20% Convallaria majalis, Dragoco Rep. 5:21(1/1996); 35.08% Daphne tangutica; 21.00% Narcissus poeticus 79



100



OH



80



108



60 40



51



20



91



65 40



60



80



100



120



RT: 8.80 AI: 1027 KI: 1032 Hexanoic acid CAS#: 4536-23-6 MF: C7 H14 O2 FW: 130 MSD LIB#: 1974 CN: hexanoic acid, 2-methylSynonyms: 2-methyl caproic acid Source: Bedoukian Res. ex JJ Brophy 74



100



OH



80 60



O



40 43



20 40



87 55 60



80



100



120



140



Appendix III: Mass Spectra



145



RT: 8.83 AI: 1028 KI: 1033 Acetyl pyridine CAS#: 1122-62-9 MF: C7 H7 N O FW: 121 MSD LIB#: 49 CN: ethanone, 1-(2-pyridinyl)Synonyms: 2-pyridyl methyl ketone Source: Aldrich Chem. 79



100



N



80



43



51



60



121



93



40 20



106 40



60



80



100



120



140



RT: 8.89 AI: 1030 KI: 1035 Thiazole CAS#: 18640-74-9 MF: C7 H11 N S FW: 141 MSD LIB#: 56 CN: thiazole, 2-(2-methylpropyl)Synonyms: 2-isobutylthiazole Source: Aldrich Chem. 99



100



N



80 S



60 58



40 20 41



126



40



60



80



100



140



120



140



RT: 8.90 AI: 1030 KI: 1035 Octen-2-one CAS#: 18402-82-9 MF: C8 H14 O FW: 126 MSD LIB#: 1941 CN: 3-octen-2-one (3E)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 55



100



E



80 43



60



O



111



40 20



97



69 40



60



80



100



126 120



140



Ac



Adams: Essential Oil Components by GC/MS



146



RT: 8.95 AI: 1031 KI: 1037 Furan CAS#: 1193-79-9 MF: C7 H8 O2 FW: 124 MSD LIB#: 724 CN: 2-acetyl-5-methylfuran Synonyms: 2-methyl-5-acetylfuran; ethanone, 1-(5-methyl-2-furanyl)Source: Aldrich Chem. 109



100 80



O O



60 43



40



53



124



20



81 40



60



80



100



120



140



RT: 8.96 AI: 1032 KI: 1037 Ocimene CAS#: 3338-55-4 MF: C10 H16 FW: 136 MSD LIB#: 165 CN: 1,3,6-octatriene, 3,7-dimethyl-, (3Z)Synonyms: cis-ocimene Source: distillation of sweet anis leaves, Calif., RP Adams #5452; 42.30% Tagetes minuta, Perf. Flav. 10:73(1985); 40.20% Tithonia diversifolia; 32.23% Cloranthus spicatus 93



100 80 60 40



41



79 53



20 40



105



67 60



80



100



RT: 8.99 AI: 1032 KI: 1038 Propyl tiglate CAS#: 61692-83-9 MF: C8 H14 O2 FW: 142 CN: 2-butenoic acid, 2-methyl-, propyl ester, (E)Synonyms: none Source: Aldrich Chem. 100



121



136



120



140



MSD LIB#: 44



83



55



O



80 O



60



101



40 20



41



127 142



40



60



80



100



120



140



Appendix III: Mass Spectra



147



RT: 9.03 AI: 1033 KI: 1039 Hexanoic acid CAS#: 628-46-6 MF: C7 H14 O2 FW: 130 MSD LIB#: 2063 CN: hexanoic acid, 5-methylSynonyms: caproic acid, 5-methyl-; isoenanthic acid Source: Bedoukian Res. 60



100



O



80 60



OH



71



43



87



40 20



97 40



60



80



100



120



140



RT: 9.04 AI: 1034 KI: 1039 Lavender lactone CAS#: 1073-11-6 MF: C7 H10 O2 FW: 126 MSD LIB#: 195 CN: 2(3H)-furanone, 5-ethenyldihydro-5-methylSynonyms: methyl hex-5-enolide ; γ-vinyl-γ-valerolactone Source: Armoise a davanone oil ex Guy Collin 43



100



55 111



80



O



67



60



O



40



83



20



98 126



40



60



80



100



120



140



RT: 9.06 AI: 1034 KI: 1040 Santolina alcohol CAS#: 35671-15-9 MF: C10 H18 O FW: 154 MSD LIB#: 232 CN: 4-hexen-2-ol, 3-ethenyl-2,5-dimethyl-, (S)Synonyms: none Source: Artemisia vestita oil ex P. Weyerstahl; 3.20% Ormenis mixta, Parfums Cosmet. Aromes 60:65(1984); 3.14% Artemisia vestita; 0.20% Artemisia judaica 59



100



OH



81



80



96



60 40



43



20



67 40



60



139 80



100



120



140



160



Adams: Essential Oil Components by GC/MS



148



RT: 9.14 AI: 1036 KI: 1042 Benzene acetaldehyde CAS#: 122-78-1 MF: C8 H8 O FW: 120 MSD LIB#: 272 CN: benzene acetaldehyde Synonyms: α-tolualdehyde; phenylethanal; phenylacetaldehyde Source: ref. cpd. ex J.P. Vidal, France 91



100



O



80 60 40



65



20



120



51 40



60



80



100



120



140



RT: 9.17 AI: 1037 KI: 1043 Rose oxide CAS#: 16665-10-4 MF: C10 H20 O FW: 156 MSD LIB#: 1365 CN: 2H-pyran, tetrahydro-4-methyl-2-(2-methylpropyl)-, (2R,4R)Synonyms: none Source: ref. cpd. ex P. Weyerstahl 99



100 80 60



43



40



O



55



20



69



81 141



40



60



80



100



120



140



156 160



RT: 9.19 AI: 1038 KI: 1043 Heptyl acetate CAS#: 5921-82-4 MF: C9 H18 O2 FW: 158 MSD LIB#: 143 CN: 2-heptanol, acetate Synonyms: hept-2-yl ethanoate Source: Amyris diatrypa oil, Dom. Rep. ex Tom Zanoni; 3.30% Aframomum melegueta, FFJ 6:183(1991); 0.10% Zingiber officinale; 0.06% Ruta angustifolia 100



43 O-Ac



80 60 40 20



87



56 40



70 60



80



98 100



120



140



160



Appendix III: Mass Spectra



149



RT: 9.20 AI: 1038 KI: 1044 Ethyl hex-(2E)-enoate CAS#: 27829-72-7 MF: C8 H14 O2 FW: 142 MSD LIB#: 682 CN: 2-hexenoic acid, ethyl ester, (E)Synonyms: ethyl trans-2-hexenoate Source: Bedoukian Res. ex Art Tucker 55



100



O



80



E



97



60 41



O



73



40 20



81 40



60



80



114 100



127 120



142 140



RT: 9.23 AI: 1039 KI: 1044 Salicylaldehyde CAS#: 90-02-8 MF: C7 H6 O2 FW: 122 MSD LIB#: 1370 CN: benzaldehyde, 2-hydroxySynonyms: 2-formylphenol Source: ref. cpd. ex Keith Harkiss; 2.50% Tagetes minuta, Indian Perf. 19:29(1975); 1.75% Cinnamomum cassia; 0.48% Cinnamomum zeylanicum 122



100 80 60 65



40 20 40



93



76



50 60



80



104 100



120



140



RT: 9.33 AI: 1042 KI: 1047 Hexalactone CAS#: 695-06-7 MF: C6 H10 O2 FW: 114 MSD LIB#: 1977 CN: 2(3H)-furanone, 5-ethyldihydroSynonyms: γ-caprolactone; hexanolide-1,4; tonkalide Source: Bedoukian Res. ex JJ Brophy; 0.23% Zizyphus jujuba fruit, JEOR 8:323(1996); 0.15% Psidium guajava fruit; 0.02% Mandragora officinarum



O



O



Adams: Essential Oil Components by GC/MS



150



RT: 9.42 AI: 1044 KI: 1050 Ocimene CAS#: 3779-61-1 MF: C10 H16 FW: 136 MSD LIB#: 894 CN: 1,3,6-octatriene, 3,7-dimethyl-, (3E)Synonyms: trans-ocimene Source: Juniperus barbadensis leaf oil RP Adams #5400; 94.80% Astronium fraxinfolium, JEOR 8:177(1996); 75.00% Narcissus pseudonarcissus; 68.59% Bouea macrophylla 93



100 80 60



79



41



40 53



20



105



67



40



60



80



121



100



136



120



140



RT: 9.45 AI: 1045 KI: 1051 Isobutyl angelate CAS#: 7779-81-9 MF: C9 H16 O2 FW: 156 MSD LIB#: 1610 CN: 2-butenoic acid, 2-methyl-, 2-methylpropyl ester (Z)Synonyms: angelic acid, isobutyl ester, crotonic acid, cis-2-methyl-2-butenoate Source: Aldrich Chem.; 37.41% Anthemis nobilis (Italy), in: Atlas of Essential Oils, Srinivas, Publ., Bronx, NY(1986); 35.92% Anthemis nobilis (Japan); 0.20% Helichrysum italicum 100



55



100



83



O



80



Z O



60 40 20



43 40



156 60



80



100



120



140



160



RT: 9.50 AI: 1046 KI: 1052 Methyl-2-cyclohexen-1-one CAS#: 1193-18-6 MF: C7 H10 O FW: 110 MSD LIB#: 1693 CN: 2-cyclohexen-1-one, 3-methylSynonyms: seudenone, MCH Source: Aldrich Chem. 82



100 80 60 54



40 20



O



40



110



67



41 60



80



100



120



Appendix III: Mass Spectra



151



RT: 9.51 AI: 1046 KI: 1052 Arbusculone CAS#: 56469-37-5 MF: C9 H14 O2 FW: 154 MSD LIB#: 229 CN: ethanone, 1-(5-ethenyltetrahydro-5-methyl-2-furanyl)-, cisSynonyms: none Source: Artemisia tridentata, SLC, UT ex RP Adams #5577



RT: 9.51 AI: 1046 KI: 1052 Tagetone CAS#: 1879-00-1 MF: C10 H18 O FW: 154 MSD LIB#: 1458 CN: 7-octen-4-one, 2,6-dimethylSynonyms: dihydrotagetone Source: Tagetes minuta oil ex E. Hethelyi, Hungary 57



100



85



80 41 69



60



O



40 97



20



139 40



60



80



100



120



RT: 9.52 AI: 1047 KI: 1052 Octen-1-ol CAS#: 20125-84-2 MF: C8 H16 O FW: 128 CN: 3-octen-1-ol, (Z)Synonyms: octenol, cis-3-; Source: Bedoukian Res. ex. JJ Brophy



154



140



160



MSD LIB#: 2175



55



100



OH



80 60 41



68



Z



81



40 20



95 40



60



80



110 100



128 120



140



Adams: Essential Oil Components by GC/MS



152



RT: 9.57 AI: 1048 KI: 1054 Prenyl isobutyrate CAS#: 76649-23-5 MF: C9 H16 O2 FW: 156 MSD LIB#: 1982 CN: isobutyric acid, 3-methyl-2-butenyl ester Synonyms: none Source: Bedoukian Res. ex JJ Brophy; 0.16% Anthemis nobilis, Proc. 11th Intl. Cong. of Ess. Oils, New Delhi, India, 4:207(1989) 69



100 80



43



O



60 O



40 53



20



156



40



60



80



100



120



140



160



RT: 9.59 AI: 1049 KI: 1054 Octen-1-al CAS#: 2548-87-0 MF: C8 H14 O FW: 126 MSD LIB#: 1938 CN: 2-octenal, (E)Synonyms: octenal, trans-2Source: Bedoukian Res. ex JJ Brophy; 0.70% Rhus coriaria, p. 81, in: Dragoco Bericht(1993); 0.06% Spondias cytherea; 0.01% Daphne genkwa 100



41



55



70



O



80 83



60 40 20



97 40



60



80



100



120



140



RT: 9.62 AI: 1049 KI: 1055 Pentyl isobutanoate CAS#: 2445-72-9 MF: C9 H18 O2 FW: 158 MSD LIB#: 311 CN: propanoic acid, 2-methyl, pentyl ester Synonyms: amyl isobutyrate; pentyl isobutyrate Source: artificial blackberry flavor, Lorann Oils 100



43



71



O



80 O



60 55



40



89



20 40



60



80



115 100



120



140



160



Appendix III: Mass Spectra



153



RT: 9.64 AI: 1050 KI: 1056 Ethyl levulinate CAS#: 539-88-8 MF: C7 H12 O3 FW: 144 CN: pentanoic acid, 4-oxo-, ethyl ester Synonyms: ethyl laevulinate; ethyl 4-oxovalerate Source: Bedoukian Res. 100



MSD LIB#: 2185



43



O



80



O



60 99



40 20



129



74



55 40



O



60



80



100



120



144 140



RT: 9.65 AI: 1050 KI: 1056 Cresol CAS#: 95-48-7 MF: C7 H8 O FW: 108 MSD LIB#: 1192 CN: phenol, 2-methylSynonyms: 2-methylphenol; 2-hydroxytoluene; o-tolulol Source: Pfaltz & Bauer; 0.28% Jasminum officinale, Univ. Cairo Bull. Fac. Pharm, 13:183(1974); 0.05% Atractylodes lancea; 0.05% Spartium junceum (absolute) 108



100



OH



80 60



79



40



90



51



20



63 40



60



80



100



RT: 9.67 AI: 1051 KI: 1056 Bergamal CAS#: 106-72-9 MF: C9 H16 O FW: 140 CN: 5-heptenal, 2,6-dimethylSynonyms: melonal; heptenal, 2,6-dimethyl-5Source: ref. cpd. ex E. von Rudloff 100



41



120



MSD LIB#: 790



82



80



67



60 40



55



20



140 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



154



RT: 9.72 AI: 1052 KI: 1058 Isopentyl butanoate CAS#: 106-27-4 MF: C9 H18 O2 FW: 158 MSD LIB#: 312 CN: butanoic acid, 3-methylbutyl ester Synonyms: isoamyl n-butyrate; isopentyl butyrate Source: artificial blackberry flavor, Lorann Oils 71



100 80



O



O



43



60 40 55



20 40



89 60



80



100



120



140



160



RT: 9.77 AI: 1053 KI: 1059 Naphthalene CAS#: 493-02-7 MF: C10 H18 FW: 138 MSD LIB#: 566 CN: naphthalene, decahydro-, transSynonyms: trans-decalin; trans-perhydronaphthalene Source: Aldrich Chem. 67



100 80



138



41



82



60



96



55



40



109



20 40



60



80



100



120



140



RT: 9.78 AI: 1054 KI: 1059 Terpinene CAS#: 99-85-4 MF: C10 H16 FW: 136 MSD LIB#: 994 CN: 1,4-cyclohexadiene, 1-methyl-4-(1-methylethyl)Synonyms: crithmene; moslene; p-mentha-1,4-diene Source: Lemon oil, Lorann Oils; 58.50% Satureja hortensis, J. HRC & CC 5:182(1982); 35.30% Citrus unshiu; 32.00% Citrus medica 93



100 80 60 77



40



121



43



20



51 40



105



65 60



136



80



100



120



140



Appendix III: Mass Spectra



155



RT: 9.79 AI: 1054 KI: 1060 Acetylpyrrole CAS#: 1072-83-9 MF: C6 H7 N O FW: 109 CN: ethanone, 1-(1H-pyrrol-2-yl)Synonyms: 2-pyrrolylethanone Source: Aldrich kit #2



MSD LIB#: 48



94



100 80



H



66



N



109



Ac



60 40 43



20



53



40



60



80



100



120



RT: 9.84 AI: 1055 KI: 1061 Methyl cyclohexylcarboxylate CAS#: 4630-82-4 MF: C8 H14 O2 FW: 142 MSD LIB#: 1706 CN: cyclohexanecarboxylic acid, methyl ester Synonyms: methyl cyclohexanoate Source: Aldrich Chem. 55



100



O



O-Me



80 41 60



83



40



67



20 40



60



74



101 80



100



142



113



127 120



140



RT: 9.88 AI: 1056 KI: 1062 Artemisia ketone CAS#: 546-49-6 MF: C10 H16 O FW: 152 MSD LIB#: 223 CN: 1,5-heptadien-4-one, 3,3,6-trimethylSynonyms: none Source: Artemisia tridentata, SLC, UT ex RP Adams #5577; 64.00% Artemisia annua, Toleva etal. paper #117, VIth Intl. Cong. of Ess. Oils, San Francisco(1974); 46.00% Artemisia pontica; 45.00% Santolina chamaecyparissus O



Adams: Essential Oil Components by GC/MS



156



RT: 9.89 AI: 1057 KI: 1062 Thiophene CAS#: 1455-20-5 MF: C8 H12 S FW: 140 MSD LIB#: 1480 CN: thiophene, 2-butylSynonyms: none Source: ref. cpd. ex Art Tucker 97



100



S



80 60 40 45



20



140



53



40



60



80



100



120



140



RT: 9.92 AI: 1057 KI: 1063 Benzene methanol CAS#: 98-85-1 MF: C8 H10 O FW: 122 MSD LIB#: 274 CN: benzenemethanol, α-methylSynonyms: α-phenethyl alcohol; phenylmethylcarbinol; styralyl alcohol Source: Aldrich Chem. ex Art Tucker 79



100



107



80 60



43



40



51



122



20



63 40



60



80



100



120



140



RT: 9.95 AI: 1058 KI: 1064 Norbornene-2-methanol CAS#: 67671-05-0 MF: C8 H12 O FW: 124 MSD LIB#: 1184 CN: bicyclo(2,2,1)hept-5-ene-2-methanol, (1R-exo)Synonyms: none Source: ref. cpd. ex E. von Rudloff OH



Appendix III: Mass Spectra



157



RT: 9.99 AI: 1059 KI: 1065 Acetophenone CAS#: 98-86-2 MF: C8 H8 O FW: 120 MSD LIB#: 658 CN: phenylethanone Synonyms: phenyl methyl ketone; acetylbenzene; hypnone; phenylethanone Source: Englemann spruce leaf oil ex E. von Rudloff; 20.00% Philadelphus coronarius, p. 57, in: Progress in Essential Oil Research (Proc. Intern. Symp. on Ess. Oils), E.-J. Brunke, Ed., Gruyter Publ., Berlin(1986); 2.40% Trifolium pratense (red flower); 2.20% Cistus ladaniferus (leaf) 105



100



O



77



80 60 40



51



120



43



20



68 40



60



80



100



120



140



RT: 10.00 AI: 1060 KI: 1065 Isobutyl acetoacetate CAS#: 7779-75-1 MF: C8 H14 O3 FW: 158 MSD LIB#: 1608 CN: butanoic acid, 3-oxo-, 2-methylpropyl ester Synonyms: none Source: Aldrich Chem. 100



43 O



O



80 O



60 85



40



57



40



103



69



20 60



80



100



120



140



160



RT: 10.02 AI: 1060 KI: 1065 Hexenyl oxy-acetaldehyde CAS#: 68133-72-2 MF: C8 H14 O2 FW: 142 MSD LIB#: 2124 CN: acetaldehyde, ((3Z)-3-hexenyloxy)Synonyms: none Source: Bedoukian Res. 100



41



O



55



Z



80 60



82



67



40 20



73 40



60



80



100



120



140



O



Adams: Essential Oil Components by GC/MS



158



RT: 10.03 AI: 1060 KI: 1066 Octen-1-ol CAS#: 18409-17-1 MF: C8 H16 O FW: 128 CN: 2-octen-1-ol, (E)Synonyms: octenol, trans-2Source: Bedoukian Res. ex JJ Brophy



MSD LIB#: 1939



57



100



HO



E



80 60 41 40 68



20



81 95



40



60



80



128 100



RT: 10.09 AI: 1062 KI: 1067 Tolualdehyde CAS#: 529-20-4 MF: C8 H8 O FW: 120 CN: benzaldehyde, 2-methylSynonyms: 2-methylbenzaldehyde Source: Fluka Chem.



120



140



MSD LIB#: 1509



91



100



H



80



120



60



O



65



40 51



20 40



60



80



100



120



140



RT: 10.11 AI: 1063 KI: 1068 Hexadienol acetate CAS#: 57006-69-6 MF: C8 H12 O2 FW: 140 MSD LIB#: 2099 CN: 2,4-hexadien-1-ol, acetate, (2E,4E)Synonyms: sorbyl acetate Source: Bedoukian Res. 100



43



E AcO



80 60 40



79



20



53 40



69 60



140



98 80



100



120



140



E



Appendix III: Mass Spectra



159



RT: 10.11 AI: 1063 KI: 1068 Octanol CAS#: 111-87-5 MF: C8 H18 O FW: 130 MSD LIB#: 34 CN: 1-octanol Synonyms: caprylic alcohol Source: ref. cpd. ex E. von Rudloff; 14.40% Citrus sinensis, Nippon Noge. Kaishi 58:691(1984); 12.70% Boswellia carterii; 2.00% Alpinia katsumadai 100



41 56



80 60



69 84



40 20 40



60



80



100



120



140



RT: 10.12 AI: 1063 KI: 1068 Hexenyl oxy-acetaldehyde CAS#: 000-00-0 MF: C8 H14 O2 FW: 142 MSD LIB#: 2125 CN: acetaldehyde, ((3E)-3-hexenyloxy)Synonyms: none Source: Bedoukian Res. 100



41



O



E



55



O



80 60



82



67



40 20



73 40



60



80



100



120



140



RT: 10.15 AI: 1064 KI: 1069 Tolualdehyde CAS#: 620-23-5 MF: C8 H8 O FW: 120 MSD LIB#: 1508 CN: benzaldehyde, 3-methylSynonyms: 3-methylbenzldehyde Source: Fluka Chem. 91



100



H



119



80



O



60 65



40 51



20 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



160



RT: 10.20 AI: 1065 KI: 1070 Octenol CAS#: 64275-73-6 MF: C8 H16 O FW: 128 CN: 5-octen-1-ol, (5Z)Synonyms: none Source: Bedoukian Res. 100



MSD LIB#: 2055



67



Z



41



OH



80 60



81



55



40 95



20



110 128



40



60



80



100



120



140



RT: 10.20 AI: 1065 KI: 1070 Sabinene hydrate (IPP vs. OH) CAS#: 17699-16-0 MF: C10 H18 O FW: 154 MSD LIB#: 1438 CN: bicyclo(3.1.0)hexan-2-ol, 2-methyl-5-(1-methylethyl)-,(1α,2α,5α)Synonyms: trans-4-thujanol; trans-sabinene hydrate (trans for Me vs. IPP, old name) Source: Strobilanthes oil ex P. Weyerstahl; 25.00% Majorana hortensis, FFJ 2:55(1987); 21.53% Origanum rotundifolium; 10.81% Origanum micranthum 100



43 OH



80



71



H



93



60 40



81



55



111



121



20 40



60



80



100



120



139 140



154 160



RT: 10.22 AI: 1066 KI: 1070 Arbusculone CAS#: 56469-36-4 MF: C9 H14 O2 FW: 154 MSD LIB#: 230 CN: ethanone, 1-(5-ethenyltetrahydro-5-methyl-2-furanyl)-, transSynonyms: none Source: Artemisia tridentata, SLC, UT ex RP Adams #5577 100



43 55



80



Ac



111



60



93



40



67



20



81 126



40



60



80



100



120



139 140



160



O



Appendix III: Mass Spectra



161



RT: 10.23 AI: 1066 KI: 1071 Octanone CAS#: 496-77-5 MF: C8 H16 O2 FW: 144 MSD LIB#: 1597 CN: 5-hydroxy-4-octanone Synonyms: butyroin, 5-octanol-4-one Source: Aldrich Chem. 100



OH



55



43



80 60



O



73



40 20



102 40



60



80



100



120



140



RT: 10.29 AI: 1067 KI: 1072 Linalool oxide (furanoid) CAS#: 5989-33-3 MF: C10 H18 O2 FW: 170 MSD LIB#: 988 CN: 2-furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, cisSynonyms: linalool oxide B Source: Lavender oil ex Firmenich ex AF Thomas; 17.17% Magnolia purpurella, p. 204, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 14.60% Osmanthus fragrans; 11.50% Cinnamomum camphora 59



100 80



43 O



60



94



40



68



49



84



20 40



60



111



80



100



121



137143



120



140



155 OH



160



180



RT: 10.30 AI: 1068 KI: 1072 Mentha-3,8-diene CAS#: 586-67-4 MF: C10 H16 FW: 136 MSD LIB#: 587 CN: cyclohexene, 4-methyl-1-(1-methylethenyl)Synonyms: p-mentha-3,8-diene Source: Dicerandra frutescens oil ex Mark Deyrup, FL 79



100 80 60 40



93



107



41



20



65



51 40



121



60



136 80



100



120



140



Adams: Essential Oil Components by GC/MS



162



RT: 10.30 AI: 1068 KI: 1072 Norbornene-2-methanol CAS#: 67671-06-1 MF: C8 H12 O FW: 124 MSD LIB#: 1185 CN: bicyclo(2.2.1)hept-5-ene-2-methanol, (1R-endo)Synonyms: none Source: ref. cpd. ex P. Weyerstahl OH



RT: 10.31 AI: 1068 KI: 1073 Rose oxide CAS#: 140238-79-5 MF: C10 H20 O FW: 156 MSD LIB#: 1366 CN: 2H-pyran, tetrahydro-4-methyl-2-(2-methylpropyl)-, (2S,4R)Synonyms: none Source: IFF ex Jian-Qin Cu, Kunming 99



100 80 60



O



43



40



55



20



69



81 156



40



60



80



100



RT: 10.35 AI: 1069 KI: 1074 Dihydro myrcenol CAS#: 18479-58-8 MF: C10 H20 O FW: 156 CN: 7-octen-2-ol, 2,6-dimethylSynonyms: none Source: IFF ex Jian-Qin Cu, Kunming



120



140



160



MSD LIB#: 606



59



100 80 60 40



43



20



67 40



60



83 80



123 100



120



140



160



Appendix III: Mass Spectra



163



RT: 10.43 AI: 1071 KI: 1076 Benzyl formate CAS#: 104-57-4 MF: C8 H8 O2 FW: 136 MSD LIB#: 290 CN: formic acid, phenylmethyl ester Synonyms: benzyl methanoate Source: K & K ex H. Hills; 1.20% Acacia praicox (flower), FFJ 11:3(1996); 0.18% Ocimum basilicum; 0.11% Michelia alba (flower) 91



100



H



80 136



60 40



51



79



65



O



O



107



20 40



60



80



100



120



140



RT: 10.43 AI: 1071 KI: 1076 Cresol CAS#: 106-44-5 MF: C7 H8 O FW: 108 MSD LIB#: 1230 CN: phenol, 4-methylSynonyms: p-oxytoluene; p-tolulol Source: Jasmin absolute ex Firmenich ex AF Thomas; 21.60% Jasminum polyanthum, Dragoco Report 1/1996, 5-21; 3.76% Jasminum officinale (absolute); 2.86% Jasminum officinale (headspace) 107



100



OH



80 60 40



77 51



20 40



90



63 60



80



100



120



RT: 10.45 AI: 1072 KI: 1076 Cresol CAS#: 108-39-4 MF: C7 H8 O FW: 108 MSD LIB#: 1042 CN: phenol, 3-methylSynonyms: m-methylphenol; m-oxytoluene; 3-hydroxytoluene; m-tolulol Source: Fisher Sci.; 2.33% Jasminum sambac, FFJ 11:57(1996); 2.01% Narcissus tazetta; 0.45% Narcissus jonquilla 108



100



OH



80 60 79



40 51



20 40



90



63 60



80



100



120



Adams: Essential Oil Components by GC/MS



164



RT: 10.52 AI: 1074 KI: 1078 Heptanal, dimethyl acetal CAS#: 10032-05-0 MF: C9 H20 O2 FW: 160 MSD LIB#: 2113 CN: heptane, 1,1-dimethoxySynonyms: none Source: Bedoukian Res. OMe



75



100 80



MeO



60 40 20



45 40



55



129



97 60



80



100



120



140



160



180



RT: 10.61 AI: 1076 KI: 1080 Vertocitral C CAS#: 65405-78-9 MF: C9 H14 O FW: 138 MSD LIB#: 1552 CN: 3-cyclohexene-1-carboxaldehyde, 3,5-dimethyl-, cisSynonyms: dimethyl cyclohexene carboxaldehyde Source: H & R Chem. ex Jian-Qin Cu, Kunming 67



100



H



80 60



O



41 55



40



107



95



79



123



138



20 40



60



80



100



RT: 10.66 AI: 1077 KI: 1081 Tolualdehyde CAS#: 104-87-0 MF: C8 H8 O FW: 120 CN: benzaldehyde, 4-methylSynonyms: 4-methylbenzaldehyde Source: Fluka Chem.



120



140



MSD LIB#: 1510



91



100



119



80



H



60



O



65



40 20



41 40



51 60



80



100



120



140



Appendix III: Mass Spectra



165



RT: 10.70 AI: 1078 KI: 1082 Camphenilone CAS#: 13211-15-9 MF: C9 H14 O FW: 138 MSD LIB#: 820 CN: bicyclo(2.2.1)heptan-2-one, 3,3-dimethylSynonyms: 2-norbornanone, 3,3-dimethylSource: Spruce leaf oil ex E. von Rudloff and L. Hogge; 0.11% Micromeria carminea, JEOR 7:457(1995); 0.10% Artemisia alba; 0.07% Citronella ceylon 69



100 80 60



41



40



138



20



55 40



95



81 60



80



100



120



140



RT: 10.71 AI: 1079 KI: 1082 Pyrazine CAS#: 23787-80-6 MF: C7 H8 N2 O FW: 136 MSD LIB#: 1352 CN: ethanone, 1-(3-methylpyrazinyl)Synonyms: none Source: Pyrazine specialties ex Art Tucker 43



100



N



80



136



93



60 40



N



67



52



108



20 40



60



80



100



RT: 10.72 AI: 1079 KI: 1082 Allyl hexanoate CAS#: 123-68-2 MF: C9 H16 O2 FW: 156 CN: hexanoic acid, 2-propenyl ester Synonyms: allyl caproate Source: H&R ex Jian-Qin Cu, Kunming 100



120



140



MSD LIB#: 111



43 O



80 60 71



40



O



99



55



20



113 40



60



80



100



127 120



140



160



Ac



Adams: Essential Oil Components by GC/MS



166



RT: 10.76 AI: 1080 KI: 1083 Artemisia alcohol CAS#: 57590-19-9 MF: C10 H18 O FW: 154 MSD LIB#: 224 CN: 1,5-heptadien-4-ol, 3,3,6-trimethylSynonyms: none Source: Artemisia tridentata, SLC, UT ex RP Adams #5577; 24.00% Artemisia annua (Hungary), JEOR 7:45(1995); 7.50% Artemisia judaica 85



100 80 60 40 41 20



55 40



67 60



80



100



120



140



160



RT: 10.76 AI: 1080 KI: 1083 Benzene CAS#: 3558-60-9 MF: C9 H12 O FW: 136 MSD LIB#: 276 CN: benzene, (2-methoxyethyl)Synonyms: pandanol, methyl phenyl ethyl ether Source: ref. cpd. ex Jian-Qin Cu, Kunming 45



100 80 60 40



91



20



65



51 40



60



136



104



77 80



100



120



140



RT: 10.78 AI: 1081 KI: 1084 Acetyl-2,5-dimethyl furan CAS#: 10599-70-9 MF: C8 H10 O2 FW: 138 MSD LIB#: 12 CN: acetyl-2,5-dimethyl furan Synonyms: none Source: Aldrich Chem. 43



100



O



80



O



123



60 40 20 40



138



81



53



95 60



80



100



120



140



Appendix III: Mass Spectra



167



RT: 10.79 AI: 1081 KI: 1084 Pyrazine CAS#: 15707-24-1 MF: C8 H12 N2 FW: 136 MSD LIB#: 53 CN: pyraxine, 2,3-diethylSynonyms: none Source: Aldrich Chem. 121



100



136



N



80 60 40 20



N



80 41



52



107 65



40



60



80



100



120



140



RT: 10.80 AI: 1081 KI: 1084 Hexenal , diethyl acetal CAS#: 87383-46-8 MF: C10 H20 O2 FW: 172 MSD LIB#: 804 CN: 2-hexene, 1,1-diethoxy, (Z)Synonyms: 1,1-diethoxy-2Z-hexene Source: Bedoukian Res. ex Art Tucker 57



100



O-Et



Z



80



O-Et



60 40



127



85 41 69 75



20



103 143



40



60



80



100



120



172



140



160



180



RT: 10.82 AI: 1082 KI: 1085 Cymenene CAS#: 1124-20-5 MF: C10 H12 FW: 132 MSD LIB#: 426 CN: benzene, 1-methyl-3-(1-methylethenyl)Synonyms: α-3-dimethylstyrene; 2-m-tolylpropene; m-isopropenyltoluene Source: Chamaecyparis nootkatensis leaf oil ex E. von Rudloff; Identification by R. Laurent, Robertet, France 100



117



132



80 60



91



40 20



65



51 41 40



60



77 80



100



120



140



Adams: Essential Oil Components by GC/MS



168



RT: 10.86 AI: 1083 KI: 1086 Pyrazine CAS#: 1124-11-4 MF: C8 H12 N2 FW: 136 MSD LIB#: 69 CN: pyrazine, tetramethylSynonyms: ligustrazine Source: Aldrich Chem. 54



100 80 60



N



136



42



N



40 20



95 40



60



80



100



120



140



RT: 10.88 AI: 1083 KI: 1086 Fenchone CAS#: 1195-79-5 MF: C10 H16 O FW: 152 MSD LIB#: 162 CN: bicylco(2.2.1)heptan-2-one, 1,3,3-trimethylSynonyms: 2-norbornanone, 1,3,3-trimethyl-; 1,3,3-trimethylnorcamphor Source: Sweet Anis leaves (Foeniculum vulgare) distilled, RP Adams #5452; 42.10% Lavandula stoechas, 11th Intl. Cong. of Ess. Oils, Frag.& Flav., New Delhi, India 4:15(1989); 25.10% Alpinia katsumadai (stem); 24.30% Foeniculum vulgare 81



100 80 60



69



40 41 20



53 40



109 60



80



100



137 120



152



140



160



RT: 10.88 AI: 1083 KI: 1086 Furfuryl propionoate CAS#: 623-19-8 MF: C8 H10 O3 FW: 154 MSD LIB#: 81 CN: 2-furanmethanol, propanoate Synonyms: furfuryl alcohol, propionate Source: Aldrich Chem. 81



100



O O



80



O



60 40 20



98



52



154



41 40



60



80



100



120



140



160



Appendix III: Mass Spectra



169



RT: 10.89 AI: 1084 KI: 1086 Linalool oxide (furanoid) CAS#: 34995-77-2 MF: C10 H18 O2 FW: 170 MSD LIB#: 989 CN: 2-furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-,transSynonyms: linalool oxide A Source: Lavender oil ex Firmenich ex AF Thomas; 21.10% Osmanthus fragrans, Rastit. Resur. 22:243(1986); 10.80% Cinnamomum camphora; 7.89% Magnolia purpurella 59



100 80



43



60



O



94



40



68



49



20 40



60



84



111



80



100



121



137143



120



140



155 OH



160



180



RT: 10.94 AI: 1085 KI: 1088 Butyl angelate CAS#: 7785-64-0 MF: C9 H16 O2 FW: 156 MSD LIB#: 1992 CN: 2-butenoic acid, 2-methyl-, butyl ester (2Z)Synonyms: none Source: Bedoukian Res. ex J.J. Brophy; 34.90% Anthemis nobilis, Planta med. 57:237(1991) 100



100 80



55



60 40 20



O



Z O



83 41 156 40



60



80



100



120



140



160



RT: 10.94 AI: 1085 KI: 1088 Cyclohexanedione CAS#: 3008-43-3 MF: C7 H10 O2 FW: 126 MSD LIB#: 1687 CN: 1,2-cyclohexanedione,3-methylSynonyms: none Source: Aldrich Chem. 83



100



O



55



80 60



O



41



70



126



97



40 20



111 40



60



80



100



120



140



Adams: Essential Oil Components by GC/MS



170



RT: 10.94 AI: 1085 KI: 1088 Mentha-2,4(8)-diene CAS#: 586-63-0 MF: C10 H16 FW: 136 MSD LIB#: 586 CN: cyclohexene, 3-methyl-6-(1-methylethylidene)Synonyms: p-mentha-2,4(8)-diene; isoterpinolene Source: Dicerandra frutescens oil ex Mark Deyrup, FL 93



100



121



80 79



60 40



41



136 53



20



107



67



40



60



80



100



120



140



RT: 10.97 AI: 1086 KI: 1088 Acetyl thiophene CAS#: 88-15-3 MF: C6 H6 O S FW: 126 MSD LIB#: 51 CN: ethanone, 1-(2-thienyl)Synonyms: ketone, methyl 2-thienyl Source: Aldrich 111



100 80



S



60 126



40



43



20



83



57 40



60



80



100



120



140



RT: 10.98 AI: 1086 KI: 1088 Terpinolene CAS#: 586-62-9 MF: C10 H16 FW: 136 MSD LIB#: 916 CN: cyclohexene, 1-methyl-4-(1-methylethylidene)Synonyms: p-mentha-1,4(8)-diene, isoterpinene Source: Juniperus lucayana leaf oil, RP Adams #2863; 49.70% Vepris elliotii, JEOR 7:447(1995); 40.28% Protium heptaphyllum (stem); 18.91% Pistacia vera (fruit hull) 93



100



121



80



136



60



79



43



40



58



20 40



60



105



67 80



100



120



140



Ac



Appendix III: Mass Spectra



171



RT: 11.00 AI: 1087 KI: 1089 Guaiacol CAS#: 90-05-1 MF: C7 H8 O2 FW: 124 MSD LIB#: 755 CN: phenol, 2-methoxySynonyms: anastil; guaiastil; o-hydroxyanisole; o-methyl catechol; pyroguaiac acid Source: ref. cpd. ex E. von Rudloff 109



100



81



80



124



60 53



40 20



63 40



60



80



100



120



140



RT: 11.01 AI: 1087 KI: 1089 Hexenal CAS#: 51795-75-6 MF: C10 H20 O2 FW: 172 MSD LIB#: 2119 CN: 3-hexene, 1,1-diethoxy-, (3E)Synonyms: none Source: Bedoukian Res. 47



100



E



O



103



80 60



O



75



40 20



41



55 69



40



60



81



127



80



100



120



140



160



180



RT: 11.03 AI: 1087 KI: 1090 Nonanone CAS#: 821-55-6 MF: C9 H18 O FW: 142 MSD LIB#: 1167 CN: nonanone (2-) Synonyms: methyl heptyl ketone Source: K & K Chem. ex H. Hills; 24.70% Ruta graveolens, Sci. Pharm. 56:121(1988); 16.24% Ruta chalepensis 100



43



O



58



80



(CH2)6-CH3



60 40 71



20



127 40



60



80



100



120



142 140



Adams: Essential Oil Components by GC/MS



172



RT: 11.05 AI: 1088 KI: 1090 Linalool CAS#: 000-00-0 MF: C10 H16 O FW: 152 MSD LIB#: 1013 CN: not assigned Synonyms: none Source: ref. cpd. ex P. Weyerstahl 100



41



80



OH



69



55



60



119



91



40 79



20 40



60



137



109



80



100



120



140



160



RT: 11.05 AI: 1088 KI: 1090 Norbornen-2-ol acetate CAS#: 5257-37-4 MF: C9 H12 O2 FW: 152 MSD LIB#: 1182 CN: bicyclo(2.2.1)hept-5-en-2-ol, acetate, exoSynonyms: none Source: acetylation of norbornen-2-ol(6288) 66



100 80 60



43



40 20



81 40



60



91



80



152 100



120



140



160



RT: 11.07 AI: 1088 KI: 1090 Methyl benzoate CAS#: 93-58-3 MF: C8 H8 02 FW: 136 MSD LIB#: 952 CN: benzoic acid, methyl ester Synonyms: noibe oil; clorius Source: Jasmin absolute ex Firmenich ex AF Thomas; 41.21% Polianthes tuberosa, p. 109, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 32.34% Gardenia jasminoides; 23.40% Narcissus jonquilla 105



100 80



77



60 40



136



51



20 40



60



80



100



120



140



Appendix III: Mass Spectra



173



RT: 11.08 AI: 1089 KI: 1091 Pentyl butanoate CAS#: 540-18-1 MF: C9 H18 O2 FW: 158 MSD LIB#: 313 CN: butanoic acid, pentyl ester Synonyms: amyl butyrate; pentyl butyrate Source: artificial blackberry flavor, Lorann Oils; 0.03% Osmanthus fragrans, Rastit. Resur. 22:243(1986); 0.01% Spartium junceum (absolute); 0.01% Spartium junceum (headspace) 100



43



O



71



80



O



89



60 40



55



20 132 40



60



80



100



120



144 140



160



RT: 11.09 AI: 1089 KI: 1091 Cymenene CAS#: 1195-32-0 MF: C10 H12 FW: 132 MSD LIB#: 427 CN: benzene, 1-methyl-4-(1-methylethenyl)Synonyms: α-p-dimethylstyrene; dehydro-p-cymene; 4-isopropenyltoluene Source: Chamaecyparis nootkatensis leaf oil ex E. von Rudloff 117



100



132



80 60



91



40 20 41



65



51



81 105



40



60



80



100



120



140



RT: 11.11 AI: 1090 KI: 1091 Hexenyl methyl carbonate CAS#: 67633-96-9 MF: C8 H14 O3 FW: 158 MSD LIB#: 2045 CN: carbonic acid, (3Z)-3-hexenyl methyl ester Synonyms: none Source: Bedoukian Res. O



67



100



Z



80 60



82



40 41 55



20 40



60



80



100



120



140



160



O



OMe



Adams: Essential Oil Components by GC/MS



174



RT: 11.14 AI: 1090 KI: 1092 Epoxymyrcene CAS#: 29414-55-9 MF: C10 H16 O FW: 152 MSD LIB#: 1021 CN: oxirane, 2,2-dimethyl-3-(3-methylene-4-pentenyl)Synonyms: myrcene epoxide Source: Lippia multiflora oil ex C. Menut & G. Lamaty; 70.30% Lippia multiflora (leaf), FFJ 10:75(1995) 79



100 80 41



59



60



71



40



O



53



20



85



93 137



40



60



80



100



120



140



160



RT: 11.14 AI: 1090 KI: 1092 Hexenal CAS#: 73545-18-3 MF: C10 H20 O2 FW: 172 MSD LIB#: 2121 CN: 3-hexene, 1,1-diethoxy-, (Z)Synonyms: none Source: Bedoukian Res. 47



100



O



103



80



Z



60



O



75



40 20



41



55 69



40



60



81



127



80



100



120



140



160



180



RT: 11.14 AI: 1090 KI: 1092 Isopropyl-2-methoxypyrazine CAS#: 25773-40-4 MF: C8 H12 N2 O FW: 152 MSD LIB#: 1622 CN: pyrazine, 2-methoxy-3-(1-methylethyl)Synonyms: none Source: Aldrich Chem. 137



100 80



O N



60 N



40 20



152



124 42 40



68



52 60



81 80



95



105 100



120



140



160



Appendix III: Mass Spectra



175



RT: 11.15 AI: 1088 KI: 1090 Isobutyl tiglate CAS#: 61692-84-0 MF: C9 H16 O2 FW: 156 MSD LIB#: 860 CN: 2-butenoic acid, 2-methyl-, 2-methylpropyl ester, (E)Synonyms: none Source: Aldrich Chem. ex Art Tucker; 0.34% Anthemis nobilis (Japan), Koryo 161:93(1989); 0.03% Anthemis nobilis (India)



E



55



80



O



101



60 40



O



83



100



41



20 40



60



80



100



120



140



160



RT: 11.19 AI: 1092 KI: 1093 Butyl pentanoate CAS#: 591-68-4 MF: C9 H18 O2 FW: 158 MSD LIB#: 330 CN: pentanoic acid, butyl ester Synonyms: butyl valerate; valeric acid, butyl ester Source: Aldrich Chem.; 0.01% Spartium junceum, Rivista Ital. EPPOS 325-343(1992) 100



56



O



85



41



80



O



103



60 40 73



20



129 40



60



80



100



120



RT: 11.20 AI: 1092 KI: 1093 Ethyl sorbate CAS#: 2396-84-1 MF: C8 H12 O2 FW: 140 CN: 2,4-hexadienoic acid, ethyl ester, (2E,4E)Synonyms: sorbic acid, ethyl ester Source: Bedoukian Res.



160



MSD LIB#: 2149



O



67



100



140



95



E



80 41



O



60



140



40



125



20



55 40



111 60



80



100



120



140



E



Adams: Essential Oil Components by GC/MS



176



RT: 11.22 AI: 1092 KI: 1094 Norbornen-2-ol acetate CAS#: 99295-40-6 MF: C9 H12 O2 FW: 152 MSD LIB#: 1179 CN: bicyclo(2.2.1)hept-5-en-2-ol, acetate, endoSynonyms: none Source: acetylation of norbornen-2-ol(6294) 66



100 80



O-Ac



43



60 40 20



81 40



60



91



80



152 100



120



140



160



RT: 11.23 AI: 1093 KI: 1094 Pyrazine CAS#: 21948-70-9 MF: C5 H6 N2 S FW: 126 MSD LIB#: 1354 CN: pyrazine, (methylthio)Synonyms: none Source: Pyrazine Specialties ex Art Tucker 126



100 80



N



60



52



40



84



45



73



20 40



60



N



93



66



S-Me



80



111 100



120



140



RT: 11.30 AI: 1095 KI: 1096 Hexenyl propionate CAS#: 33467-74-2 MF: C9 H16 O2 FW: 156 MSD LIB#: 1946 CN: (3Z)-hexen-1-ol, propanoate Synonyms: hexenyl propionate, cis-3Source: Bedoukian Res. ex JJ Brophy; 0.37% Chamomilla recutita, Dragoco Rept. 3-31(1992); 0.16% Liquidamber formosana; 0.10% Artemisia annua 57



100



67 O



80



40



Z



82



60



O



41



20 40



60



80



100



120



140



160



Appendix III: Mass Spectra



177



RT: 11.32 AI: 1095 KI: 1096 Camphenone CAS#: 53803-33-1 MF: C10 H14 O FW: 150 MSD LIB#: 617 CN: bicyclo(2,2,1)heptan-2-one, 5,5-dimethyl-6-methyleneSynonyms: none Source: Diplotaenia cachrydifoliae ex K. Harkiss 93



100 80



108



60



O



40 20 41



77 51



65



40



135



60



80



100



120



150



140



160



RT: 11.32 AI: 1095 KI: 1096 Linalool CAS#: 78-70-6 MF: C10 H18 O FW: 154 MSD LIB#: 307 CN: dimethyl-1-6-octadien-3-ol Synonyms: none Source: distillation of black pepper, RP Adams #5448; 94.90% Cinnamomum camphora, JEOR 4:161(1992); 94.29% Cinnamomum parthenoxylum; 89.00% Michelia alba 100



71



43



80



OH



93



55



60 40



80



121



20



107 40



60



80



100



120



RT: 11.38 AI: 1097 KI: 1097 Nonenal CAS#: 2277-19-2 MF: C9 H16 O FW: 140 CN: 6-nonenal, (6Z)Synonyms: none Source: Bedoukian Res. 100



136



154



140



160



MSD LIB#: 2131



41



O



Z



80 60



55



40



67



20 40



60



81



80



122



93 100



120



140



Adams: Essential Oil Components by GC/MS



178



RT: 11.40 AI: 1097 KI: 1098 Ethyl heptanoate CAS#: 106-30-9 MF: C9 H18 O2 FW: 158 MSD LIB#: 80 CN: heptanoic acid, ethyl ester Synonyms: ethyl enanthate, ethyl heptylate, enanthic ether Source: Aldrich Chem.; 0.15% Citrus reticulata (leaf), JEOR 2:331(1990); 0.10% Narcissus tazetta (absolute); 0.10% Citrus medica (leaf) 88



100 80



43



60 60



40



70



101



113



20



129 40



60



80



100



158



120



140



160



RT: 11.40 AI: 1097 KI: 1098 Nonanol CAS#: 628-99-9 MF: C9 H20 O FW: 144 MSD LIB#: 1816 CN: 2-nonanol Synonyms: sec-nonyl alcohol Source: alcohols mix (2-OHs) ex K-H Kubeczka; 2.00% Curcuma heyneana, FFJ 7:19(1992); 1.40% Curcuma aeruginosa; 1.30% Psidium guajava 45



100



HO



80 60 40 20



69



55 40



126 60



80



100



120



140



RT: 11.41 AI: 1098 KI: 1098 Sabinene hydrate (IPP vs. OH) CAS#: 15826-82-1 MF: C10 H18 O FW: 154 MSD LIB#: 1439 CN: bicyclo(3.1.0)hexan-2-ol, 2-methyl-5-(1-methylethyl)-, (1α,2β,5α)Synonyms: cis-4-thujanol; cis-sabinene hydrate (IPP vs. Me, old name) Source: Strobilanthes oil ex P. Weyerstahl; 85.30% Mentha candicans, Ag. Biol. Chem. 42:433(1978); 26.20% Lippia ukambemsis; 10.00% Thymus pinewood 100



43 HO



80



H



71



60 40



93 81



55



111



20



121



139 154



40



60



80



100



120



140



160



Appendix III: Mass Spectra



179



RT: 11.42 AI: 1098 KI: 1098 Heptenol acetate CAS#: 1576-78-9 MF: C9 H16 O2 FW: 156 MSD LIB#: 2077 CN: 3-hepten-1-ol, acetate(3Z-) Synonyms: none Source: Bedoukian Res. 100



43



Z



AcO



80 54



60



81



40



96



67



20 40



60



80



100



120



140



160



RT: 11.42 AI: 1098 KI: 1098 Hexenal , diethyl acetal CAS#: 67746-30-9 MF: C10 H20 O2 FW: 172 MSD LIB#: 803 CN: 2-hexene, 1,1-diethoxy-, (E)Synonyms: (E)-1,1-diethoxy-2-hexene Source: Bedoukian Res. ex Art Tucker 57



100



O-Et



E



80



O-Et



127



60 85



40 41 20



69 40



60



99 80



143



100



120



140



171 160



180



RT: 11.43 AI: 1098 KI: 1098 Linalool CAS#: 78-69-3 MF: C10 H22 O FW: 158 MSD LIB#: 1475 CN: 3-octanol, 3,7-dimethylSynonyms: 2,6-dimethyl-6-octanol Source: SCM Chem. ex H. Hills 73



100 80 60 40



43



55



20



111 40



60



80



100



129 120



143 140



160



Adams: Essential Oil Components by GC/MS



180



RT: 11.44 AI: 1099 KI: 1099 Dimethyl styrene CAS#: 27576-03-0 MF: C10 H12 FW: 132 MSD LIB#: 612 CN: benzene, ethenyl-, dimethyl deriv. Synonyms: dimethylstyrol Source: Aldrich Chem. 117



100 80



132



60 40



91 51



20



77



65



40



60



105 80



100



RT: 11.45 AI: 1099 KI: 1099 Pinene oxide CAS#: 1686-14-2 MF: C10 H16 O FW: 152 CN: 3-oxatricyclo(4.1.1.02,4)octane, 2,7,7-trimethylSynonyms: 2,3-epoxypinane Source: ref. cpd. ex Tom Phillips, FSU



120



140



MSD LIB#: 1302



67



100



O



80 41 60 40



109



83



55



93



137



20



119 40



60



80



100



120



152 140



160



RT: 11.46 AI: 1099 KI: 1099 Naphthalene CAS#: 493-01-6 MF: C10 H18 FW: 138 MSD LIB#: 567 CN: naphthalene, decahydro-, cisSynonyms: cis-decalin; cis-perhydronaphthalene Source: Aldrich Chem. 67



100 80 60



H



81 96



138



41 55



40



H



109



20 40



60



80



100



120



140



Appendix III: Mass Spectra



181



RT: 11.48 AI: 1100 KI: 1100 Undecane CAS#: 1120-21-4 MF: C11 H24 FW: 156 MSD LIB#: 90 CN: undecane Synonyms: hendecane Source: Alltech Assoc.; 13.30% Acacia praecox, FFJ 11:3(1996); 7.50% Pittosporum tobira; 6.75% Cymbidium sinense 100



43



57



80 60



71



40



85



20



98 40



60



80



156



127



100



120



RT: 11.49 AI: 1100 KI: 1100 Ipsenol CAS#: 35628-05-8 MF: C10 H18 O FW: 154 CN: 7-octen-4-ol, 2-methyl-6-methyleneSynonyms: none Source: ref. cpd. ex Tom Phillips, FSU



140



160



MSD LIB#: 849



68



100 80 41 60 40 57



20



85 79



40



60



93



80



136 100



120



140



160



RT: 11.49 AI: 1100 KI: 1100 Isopentyl 2-methyl butanoate CAS#: 27625-35-0 MF: C10 H20 O2 FW: 172 MSD LIB#: 871 CN: butanoic acid, 2-methyl, 3-methylbutyl ester Synonyms: isoamyl 2-methyl butanoate; isopentyl 2-methyl butyrate Source: ref. cpd. ex Art Tucker 70



100 80



43



O



57 O



60 85



40



103



20



129 40



60



80



100



120



144 140



160



180



Adams: Essential Oil Components by GC/MS



182



RT: 11.50 AI: 1100 KI: 1100 Methyl butyl-2-methyl butyrate CAS#: 2445-78-5 MF: C10 H20 O2 FW: 172 MSD LIB#: 1698 CN: butanoic acid, 2-methyl-, 2-methylbutyl ester Synonyms: none Source: Aldrich Chem.; 12.00% Anthemis nobilis, Essenze Deriv. Agrum. 93:107(1973); 0.54% Myrtus communis (unripe fruit); 0.40% Achillea wilhelmsii (Egypt) 57



100



85



70



O



80 60



O



43



40 103



20



144 40



60



80



100



120



140



160



180



RT: 11.50 AI: 1102 KI: 1103 Perillene CAS#: 539-52-6 MF: C10 H14 O FW: 150 MSD LIB#: 362 CN: furan, 3-(4-methyl-3-pentenyl)Synonyms: none Source: carrot seed oil ex Nestle ex A Chainteau; 2.70% Erigeron canadensis, JEOR 4:227(1992); 0.72% Rosa damascena; 0.40% Abies holophylla 100



41



O



69



80



81



60 40



53



150



20



135



94 40



60



80



100



120



140



160



RT: 11.51 AI: 1100 KI: 1100 Nonanal CAS#: 124-19-6 MF: C9 H18 O FW: 142 MSD LIB#: 39 CN: 1-nonanal Synonyms: pelargonaldehyde Source: ref. cpd. ex E. von Rudloff; 16.63% Fragaria x ananassa (leaf), JEOR 5:105(1993); 7.29% Ligustrum sinense (flower); 4.90% Carum carvi 100



41



O



57



80 60 40



70



20



82



98 114



40



60



80



100



120



140



(CH2)7-CH3



Appendix III: Mass Spectra



183



RT: 11.53 AI: 1101 KI: 1101 Hexyl propanoate CAS#: 2445-76-3 MF: C9 H18 02 FW: 158 MSD LIB#: 1659 CN: Propanoic acid, hexyl ester Synonyms: Hexyl propionate Source: Aldrich Chem.; 0.20% Hibiscus abelmoschus, FFJ 7:65(1992); 0.17% Chamomilla recutita; 0.06% Lavandula x hybrida 57



100 80



O



41



O



60 75



40



84



69



20



129 40



60



80



100



120



140



160



RT: 11.56 AI: 1101 KI: 1102 Heptenyl acetate CAS#: 83540-70-9 MF: C9 H16 O2 FW: 156 MSD LIB#: 794 CN: 2-hepten-1-ol, acetate, (Z)Synonyms: none Source: Bedoukian Res. ex Art Tucker 100



43



Z Ac-O



80 60 40



54



20



67 40



60



81



96



80



114



100



120



140



160



RT: 11.56 AI: 1101 KI: 1102 Thujone CAS#: 546-80-5 MF: C10 H16 O FW: 152 MSD LIB#: 1497 CN: 4-methyl-1-(methylethyl)bicyclo(3.1.0)-hexane-3-one Synonyms: α-thujone Source: ref. cpd. ex E. von Rudloff 81



100 41



H



67



80



110



60



95



55



40 20



137 40



60



80



100



120



140



152 160



O



Adams: Essential Oil Components by GC/MS



184



RT: 11.58 AI: 1102 KI: 1102 Phenyl propanal CAS#: 93-53-8 MF: C9 H10 O FW: 134 MSD LIB#: 1349 CN: benzene acetaldehyde, α-methylSynonyms: phenylpropionaldehyde, α-; cumene aldehyde; hyacinthal; hydrotropic aldehyde Source: Givaudan ex H. Hills 105



100



O



80 60 40



79



20



51



134



91



40



60



80



100



120



140



RT: 11.59 AI: 1102 KI: 1103 Octadienal CAS#: 30361-28-5 MF: C8 H12 O FW: 124 MSD LIB#: 2153 CN: 2,4-octadienal, (2E,4E)Synonyms: trans, trans-octadienal Source: Bedoukian Res. 81



100



E



E



O



80 60 40 41 53



20



67



40



124



95



60



80



100



RT: 11.60 AI: 1102 KI: 1103 Disulfide, dipropyl CAS#: 629-19-6 MF: C6 H14 S2 FW: 150 CN: disulfide, dipropyl Synonyms: propyl sulfide, dipropyl sulfide Source: Aldrich Chem. 100



120



140



MSD LIB#: 1694



41



S S



80



150



60 108



40 20



58 64 40



60



73 79 80



100



120



140



160



Appendix III: Mass Spectra



185



RT: 11.60 AI: 1102 KI: 1103 Isopentyl isovalerate CAS#: 659-70-1 MF: C10 H20 O2 FW: 172 MSD LIB#: 922 CN: butanoic acid, 3-methyl-, 3-methyl butyl ester Synonyms: isoamyl isovalerate Source: Juniperus monticola f. compacta leaf oil, RP Adams #2580 70



100 80



O



43



60



O



85



57



40 20



95 40



60



80



103



113



100



131 120



150 159 169 140



160



180



RT: 11.62 AI: 1103 KI: 1103 Octadienal CAS#: 590-71-6 MF: C10 H16 O FW: 152 MSD LIB#: 1203 CN: 3,4-octadienal, 2,2-dimethylSynonyms: none Source: ref. cpd. ex E. Von Rudloff 100



43



123



95



80



O



81



60



67



55



40 20



109 40



60



80



100



137 120



140



160



RT: 11.65 AI: 1103 KI: 1104 Hexenyl propanoate CAS#: 53398-80-4 MF: C9 H16 O2 FW: 156 MSD LIB#: 1953 CN: 2-hexen-1-ol, propanoate, (E)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 57



100



O



80



O



60 40 67



20 41 40



60



82 80



127 100



120



156 140



160



E



Adams: Essential Oil Components by GC/MS



186



RT: 11.65 AI: 1103 KI: 1104 Methyl butyl isovalerate CAS#: 2445-77-4 MF: C10 H20 O2 FW: 172 MSD LIB#: 1689 CN: butanoic acid, 3-methyl-,2-methylbutyl ester Synonyms: isovaleric acid, 2-methylbutyl ester Source: Aldrich Chem. 85



100



O



80 60 40



70 57



O



43



20



103 40



60



80



130



100



142



120



140



160



180



RT: 11.66 AI: 1104 KI: 1104 Isopropyl-5-methyl-(2E)-hexenal CAS#: 69104-96-7 MF: C10 H18 O FW: 154 MSD LIB#: 1626 CN: 2-hexenal, 5-methyl-2-(1-methylethyl)-, (2E)Synonyms: isodihydrolavandulyl aldehyde Source: Aldrich Chem. 100



43



97 55



80



E



111



69



O



139



60 121



83



40 20



154 40



60



80



100



120



140



160



RT: 11.69 AI: 1104 KI: 1105 Fenchocamphorone CAS#: 40550-41-2 MF: C9 H14 O FW: 138 MSD LIB#: 711 CN: bicyclo(2.2.1)heptan-2-one, 7,7-dimethyl-, (1R,4R)Synonyms: none Source: ref. cpd. ex Y. Yuasa, Japan 69



100



O



80 41 60 40



81



55



138



95



20



110 40



60



80



100



120



140



Appendix III: Mass Spectra



187



RT: 11.72 AI: 1105 KI: 1106 Vertocitral C CAS#: 65405-79-0 MF: C9 H14 O FW: 138 MSD LIB#: 1553 CN: 3-cyclohexene-1-carboxaldehyde, 3,5-dimethyl-, transSynonyms: dimethyl cyclohexene carboxaldehyde Source: H & R Chem. ex Jian-Qin Cu, Kunming 67



100



H



80 O



60 41



55



40



95



81



107 123



20 40



60



80



100



120



138 140



RT: 11.74 AI: 1106 KI: 1107 Dimethyl phenol CAS#: 576-26-1 MF: C8 H10 O FW: 122 MSD LIB#: 750 CN: phenol, 2,6-dimethylSynonyms: 2,6-xylenol Source: Grob mixture for GC, Alltech Assoc.; 0.28% Osmanthus fragrans, Rastit. Resur. 22:243(1986) 107



100



122



80 60



77



40 20 41



91



51



40



65 60



80



100



120



140



RT: 11.80 AI: 1107 KI: 1108 Phenyl ethyl alcohol CAS#: 60-12-8 MF: C8 H10 O FW: 122 MSD LIB#: 1362 CN: benzene ethanol Synonyms: benzyl ethanol Source: Rose oil ex Firmenich ex AF Thomas 91



100 80 60 40



122



65



20



51 40



77 60



80



100



120



140



Adams: Essential Oil Components by GC/MS



188



RT: 11.77 AI: 1106 KI: 1108 Leaf alcohol CAS#: 28069-74-1 MF: C10 H20 O2 FW: 172 MSD LIB#: 2116 CN: 3-hexene, 1-(1-ethoxyethoxy)-, (3Z)Synonyms: leaf acetal Source: Bedoukian Res. 73



100



O



45



80



Z



O



60 40



55



20



83



67 40



127



60



80



100



120



140



160



180



RT: 11.77 AI: 1106 KI: 1108 Maltol CAS#: 118-71-8 MF: C6 H6 O3 FW: 126 MSD LIB#: 1043 CN: 4H-pyran-4-one, 3-hydroxy-2-methylSynonyms: larixic acid; palatone; veltol Source: ref. cpd. ex Guy Collin; 8.20% Trifolium pratense, J. Ag. Food Chem. 44:1827(1996); 5.30% Trifolium repens; 0.44% Abies balsamea 126



100



O



43



80



71



60



OH



55 O



40



97



20 40



60



80



100



120



140



RT: 11.77 AI: 1106 KI: 1108 Rose oxide CAS#: 4610-11-1 MF: C10 H18 O FW: 154 MSD LIB#: 729 CN: 2H-pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2R,4S)Synonyms: rose oxide levo Source: Geranium absolute ex Firmenich ex AF Thomas; 2.39% Pelargonium graveolens, Acta Pharm. Sinica 24:336(1989); 1.34% Citrus sinensis (leaf); 0.50% Cistus ladaniferus 139



100 80



69



60 40



41



55



83



20



97 40



60



80



100



154



131 120



140



160



Appendix III: Mass Spectra



189



RT: 11.80 AI: 1107 KI: 1108 Acrolein CAS#: 39511-08-5 MF: C7 H6 O2 FW: 122 MSD LIB#: 2030 CN: 2-propenal, 3-(2-furanyl)-, (2E)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 122



100 65



80



O



E



Me-O



O-Me



94



60 40 20



51 40



60



80



100



120



140



RT: 11.86 AI: 1108 KI: 1110 Menthatriene CAS#: 18368-95-1 MF: C10 H14 FW: 134 MSD LIB#: 1236 CN: 1,3-cyclohexadiene, 1-methyl-4-(1-methylethenyl)Synonyms: none Source: distillation of fresh parsley, RP Adams #5440; 64.70% Petroselinum crispum, J. Ag. Food Chem. 36:467(1988); 24.64% Petroselinum sativum (herb); 2.30% Apium graveolens 91



100



119



80



134



60 40 41 51



20



105



77 65



40



60



80



100



120



140



RT: 11.90 AI: 1109 KI: 1111 Benzaldehyde, dimethyl acetal CAS#: 1125-88-8 MF: C9 H12 O2 FW: 152 MSD LIB#: 268 CN: benzene, (dimethoxymethyl)Synonyms: phenyl dimethoxymethane; dimethoxyphenylmethane Source: Bedoukian Res. ex Art Tucker 121



100 80 60



77



40



91



51



20



105 152



40



60



80



100



120



140



160



O



Adams: Essential Oil Components by GC/MS



190



RT: 11.95 AI: 1110 KI: 1112 Octen-3-yl acetate CAS#: 2442-10-6 MF: C10 H18 O2 FW: 170 MSD LIB#: 1206 CN: 1-octen-3-ol, acetate Synonyms: octen-3-ol acetate, 1Source: ref. cpd. ex Art Tucker; 3.00% Lavandula angustifolia (Nana Alba), Perf. & Flav. 9:49(1984);1.60% Lavandula angustifolia (Twickel Purple); 0.63% Lepechinia urbanii 100



43



80 60 40 54



20 40



67



99



81



60



80



128



100



120



140



160



180



RT: 11.98 AI: 1111 KI: 1113 Camphenol CAS#: 3570-04-5 MF: C10 H16 O FW: 152 MSD LIB#: 618 CN: bicyclo(2.2.1)heptan-2-ol, 5,5-dimethyl-6-methyleneSynonyms: nojigikuol; 6-hydroxycamphene Source: Diplotaenia cachrydifoliae ex K. Harkiss 93



100



108



80 60 40 20



HO



41



77 53 59 65



40



60



119 80



100



120



137 140



160



RT: 11.99 AI: 1111 KI: 1113 Heptenyl acetate CAS#: 16939-73-4 MF: C9 H16 O2 FW: 156 MSD LIB#: 793 CN: 2-hepten-1-ol, acetate, (E)Synonyms: trans-2-heptenyl acetate Source: Bedoukian Res. ex Art Tucker 100



43



E Ac-O



80 60 40



54



20



67 40



60



81 80



96 100



114 120



140



160



Appendix III: Mass Spectra



191



RT: 12.00 AI: 1112 KI: 1114 Isopropyl-5-methyl-(2Z)-hexenal CAS#: 69104-97-8 MF: C10 H18 O FW: 154 MSD LIB#: 1627 CN: 2-hexenal, 5-methyl-2-(1-methylethyl)-, (Z)Synonyms: none Source: Aldrich Chem. 111



100 80



43 55



60 40



Z



97



69



121



79



20



154



105 40



60



80



100



O



139



120



140



160



RT: 12.00 AI: 1112 KI: 1114 Thujone CAS#: 471-15-8 MF: C10 H16 O FW: 152 MSD LIB#: 1496 CN: bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S-(1α,4β,5α)Synonyms: β-thujone Source: ref. cpd. ex E. von Rudloff 81



100 41



110



67



80 60



H



95



O



55



40 20



137 40



60



80



100



120



140



152 160



RT: 12.02 AI: 1112 KI: 1114 Heptyl acetate CAS#: 112-06-1 MF: C9 H18 O2 FW: 158 MSD LIB#: 780 CN: acetic acid, heptyl ester Synonyms: heptyl ethanoate Source: acetylation of heptanol(6209); 0.10% Narcissus poeticus (absolute), FFJ 9:159(1994); 0.09% Zingiber officinale; 0.03% Heracleum platytaenium 100



43



O-Ac



80 60 40



56



70



20



98 40



60



80



100



120



140



160



Adams: Essential Oil Components by GC/MS



192



RT: 12.03 AI: 1112 KI: 1114 Butanoate, 3-methyl-3-butenyl CAS#: 54410-94-5 MF: C10 H18 O2 FW: 170 MSD LIB#: 144 CN: butanoic acid, 3-methyl-, 3-methyl-3-butenyl ester Synonyms: 3-methyl-3-butenyl-isovalerate Source: Amyris diatrypa oil, Dom. Rep. ex Tom Zanoni 68



100 80



O



41 O



60



57



40



85



20



79 40



60



131



80



100



120



164



152 140



160



180



RT: 12.07 AI: 1113 KI: 1116 Octadienol CAS#: 18409-20-6 MF: C8 H14 O FW: 126 MSD LIB#: 2104 CN: 2,4-octadien-1-ol, (2E,4E)Synonyms: none Source: Bedoukian Res. 100



41



E



55



83



80



OH



67



60 40



126



20



97 40



60



80



108



100



RT: 12.10 AI: 1114 KI: 1116 Fenchol CAS#: 14575-74-7 MF: C10 H18 O FW: 154 CN: bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, endoSynonyms: α-fenchol Source: K & K Chem. ex H. Hills



120



140



MSD LIB#: 712



81



100 80 60



43



40



69



55



93



20 40



60



80



E



111 100



121 120



139 140



154 160



Appendix III: Mass Spectra



193



RT: 12.25 AI: 1117 KI: 1120 Sabina ketone CAS#: 36262-12-1 MF: C9 H12 O FW: 136 MSD LIB#: 214 CN: bicyclo(3.1.0)hex-3-en-2-one, 5-(1-methylethyl)Synonyms: lebaicone Source: Artemisia perscia oil ex P. Weyerstahl O



93



100 80



77 121



60 40 41



65



51



20 40



108



60



80



100



RT: 12.27 AI: 1118 KI: 1121 Isophorone CAS#: 78-59-1 MF: C9 H14 O FW: 138 CN: 2-cyclohexen-1-one, 3,5,5-trimethylSynonyms: isoacetophorone Source: ref. cpd. ex Z. Fleisher



136 120



140



MSD LIB#: 968



82



100 80 60 40



O



20 41



54



138 67



40



95



60



80



100



RT: 12.28 AI: 1118 KI: 1121 Fenchol CAS#: 22627-95-8 MF: C10 H18 O FW: 154 CN: bicyclo(2,2,1)heptan-2-ol, 1,3,3-trimethyl-, exoSynonyms: β-fenchol Source: K & K Chem. ex H. Hills



120



140



MSD LIB#: 713



81



100 80 60



43



40



69



55



93



20 40



60



80



111 100



121 120



139 140



154 160



Adams: Essential Oil Components by GC/MS



194



RT: 12.29 AI: 1118 KI: 1121 Menth-2-en-1-ol CAS#: 29803-82-5 MF: C10 H18 O FW: 154 MSD LIB#: 1056 CN: 2-cyclohexen-1-ol, 1-methyl-4-(1-methylethyl)-, cisSynonyms: none Source: distillation of Marjoram leaves (Schilling), RP Adams#5425 100



43 OH



80 60 40



71



55



20 40



93



79



60



80



111



100



139



121



154



120



140



160



RT: 12.30 AI: 1119 KI: 1122 Ethyl hexanoic acid CAS#: 149-57-5 MF: C8 H16 O2 FW: 144 MSD LIB#: 751 CN: hexanoic acid, 2-ethylSynonyms: 2-ethyl caproic acid; butyl ethyl acetic acid Source: Grob mixture for G, Alltech Assoc.; 0.10% Lawsonia inermis (flower), JEOR 7:425(1995); 0.02% Hedychium coronarium; 0.01% Malus arnoldiana 73



100



88



80 60



41



40



57



20



101 40



60



80



116



100



138



120



140



RT: 12.32 AI: 1119 KI: 1122 Myrcenol CAS#: 543-39-5 MF: C10 H18 O FW: 154 MSD LIB#: 1118 CN: 7-octen-2-ol, 2-methyl-6-methyleneSynonyms: none Source: IFF ex Suzanne Kral; 1.40% Elsholtzia blanda, Proc. Intl. Cong. of Ess. Oils, New Delhi, India 4:49(1989); 1.12% Hyssopus officinalis; 0.70% Viburnum orientale (leaf) 59



100 80 60



43 79



40



93



68 53



20 40



107 60



80



100



121 120



136 140



160



Appendix III: Mass Spectra



195



RT: 12.33 AI: 1119 KI: 1122 Mentha-2,8-dien-1-ol CAS#: 7212-40-0 MF: C10 H16 O FW: 152 MSD LIB#: 1069 CN: 2-cyclohexen-1-ol, 1-methyl-4-(1-methylethenyl)-, transSynonyms: none Source: ref. cpd. ex Guy Collin 100



43



OH



80



79



60 40



67



55



20



109



94



121



137 152



40



60



80



100



120



140



160



RT: 12.33 AI: 1119 KI: 1122 Pinene hydrate CAS#: 4948-29-2 MF: C10 H18 O FW: 154 MSD LIB#: 1300 CN: bicyclo(3.1.1)heptan-2-ol, 2,6,6-trimethyl-, (1α,2β,5α)Synonyms: pinan-2-ol Source: ref. cpd. ex E. von Rudloff 100



43 OH



80 60



93



71



40



55



99



81



20



111 40



60



80



100



121 136 120



140



160



RT: 12.35 AI: 1120 KI: 1123 Octanol acetate CAS#: 4864-61-3 MF: C10 H20 O2 FW: 172 MSD LIB#: 1254 CN: 3-octanol, acetate Synonyms: none Source: acetylation of peppermint oil(5498) 100



43



80



O-Ac



60 40 20



55 40



70 60



83 80



101 100



112



131 120



143 140



160



180



Adams: Essential Oil Components by GC/MS



196



RT: 12.40 AI: 1121 KI: 1124 Ethyl 3-hydroxy hexanoate CAS#: 2305-25-1 MF: C8 H16 O3 FW: 160 MSD LIB#: 2146 CN: hexanoic acid, 3-hydroxy-, ethyl ester Synonyms: caproic acid, β-hydroxy-, ethyl ester Source: Bedoukian Res. 100



117



43



O



71



80



OH



O



60 40



89



55



97



20



131 40



60



80



100



120



142 140



159 160



180



RT: 12.45 AI: 1122 KI: 1125 Rose oxide CAS#: 5258-11-7 MF: C10 H18 O FW: 154 MSD LIB#: 727 CN: 2H-pyran-, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2R-trans)Synonyms: none Source: Geranium absolute ex Firmenich ex AF Thomas; 3.54% Pelargonium graveolens, p. 317, in: Flav. & Frag.: A World Persp., Lawrence, etal., Proc. 10th Intl. Cong. of Ess. Oils, Elsevier, Amsterdam(1988); 0.82% Cistus paradisi; 0.20% Citrus sinensis 139



100 69



80 60



41



40



55



83



20 40



60



80



100



120



RT: 12.45 AI: 1122 KI: 1125 Undecyne CAS#: 2243-98-3 MF: C11 H20 FW: 152 CN: 1-undecyne Synonyms: none Source: Pfaltz & Bauer ex Art Tucker 100



154



131 140



160



MSD LIB#: 1526



41 67



80



CH2(CH2)7CH3



81



55



60 40



95



20



109 40



60



80



100



120



140



160



Appendix III: Mass Spectra



197



RT: 12.46 AI: 1122 KI: 1126 Campholenal CAS#: 4501-58-0 MF: C10 H16 O FW: 152 MSD LIB#: 903 CN: 3-cyclopentene-1-acetaldehyde, 2,2,3-trimethylSynonyms: α-campholenaldehyde Source: Juniperus gamboana ex RP Adams #2574; common in Juniperus species and other conifers 108



100 93



80 60 40 41



67 77



55



20



137 40



60



80



100



120



152



140



160



RT: 12.50 AI: 1123 KI: 1127 Methyl octanoate CAS#: 111-11-5 MF: C9 H18 O2 FW: 158 MSD LIB#: 1105 CN: octanoic acid, methyl ester Synonyms: methyl caprylate Source: Aldrich Chem.; 2.81% Psidium guajava, p. 221, in: Aromatic Plants and Essential Constituents, Peace Book Co., Hong Kong(1993); 2.17% Schinus molle (berry); 1.78% Magnolia grandiflora 74



100



O



80 60 40



O



43



87 55



20 40



60



80



127



115



101 100



120



140



160



RT: 12.53 AI: 1124 KI: 1127 Chrysanthenone CAS#: 473-06-3 MF: C10 H14 O FW: 150 MSD LIB#: 239 CN: bicyclo(3.1.1)hept-2-en-6-one, 2,7,7-trimethylSynonyms: 2-pinen-7-one (= old CAS name), 2-pinen-6-one (terpene numbering system) Source: Artemisia vestita ex P. Weyerstahl; 6.84% Artemisia judaica (Egypt), JEOR 2:271(1990); 6.30% Artemisia judaica (Israel); 4.20% Artemisia herba 107



100 80



91



60 40 20



41 40



79



122



65



53 60



O



135 80



100



120



140



150 160



Adams: Essential Oil Components by GC/MS



198



RT: 12.54 AI: 1124 KI: 1128 Stemone CAS#: 22457-23-4 MF: C8 H17 N O FW: 143 CN: 3-heptanone, 5-methyl-, oxime Synonyms: 5-methyl-3-heptanone oxime Source: Givaudan ex Jian-Qin Cu, Kunming



MSD LIB#: 1434



87



100 80



N-OH



60 40 41 56



20 40



70



114



60



80



100



128 120



140



RT: 12.55 AI: 1124 KI: 1128 Norborneol acetate CAS#: 54325-11-0 MF: C9 H14 O2 FW: 154 MSD LIB#: 1180 CN: bicyclo(2.2.1)heptan-2-ol, acetate, endoSynonyms: none Source: acetylation of norborneol, (6300) 100



43 O-Ac



80 60 40



66



20



79



55 40



60



94



80



111 100



126 120



140



160



RT: 12.59 AI: 1125 KI: 1129 Norborneol acetate CAS#: 54325-10-9 MF: C9 H14 O2 FW: 154 MSD LIB#: 1189 CN: bicyclo(2.2.1)heptan-2-ol, acetate, exoSynonyms: none Source: acetylation of norborneol (6277) 100



43 O-Ac



80 60 66



40 20



79



55 40



60



80



94 111 100



126 120



139 140



160



Appendix III: Mass Spectra



199



RT: 12.64 AI: 1127 KI: 1130 Octyl formate CAS#: 112-32-3 MF: C9 H18 O2 FW: 158 MSD LIB#: 1210 CN: formic acid, octyl ester Synonyms: none Source: Pfaltz & Bauer ex Art Tucker; 0.81% Dendranthema vestitum (flower absolute), p. 95, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993) 100



41



H



O(CH2)7CH3



56



80



O



60



70 84



40 20 40



60



80



100



120



140



160



RT: 12.68 AI: 1127 KI: 1131 Butyl tiglate CAS#: 7785-66-2 MF: C9 H16 O2 FW: 156 MSD LIB#: 2143 CN: 2-butenoic acid, 2-methyl, butyl ester, (2E)Synonyms: butyl α-methylcrotonate Source: Bedoukian Res.; 0.15% Lavandula x hybrida, p. 365, in: Lavende et Lavandin, R. Naef, Rivista Ital. EPPOS(1992); 0.12% Anthemis nobilis; 0.11% Anthemis angustifolia 55



100



O



101



83



80



E



O



60 40 41 20



141 40



60



80



100



120



140



156 160



RT: 12.70 AI: 1128 KI: 1132 Ocimene CAS#: 7216-56-0 MF: C10 H16 FW: 136 MSD LIB#: 1199 CN: 2,4,6-octatriene, 2,6-dimethyl-, (E,Z)Synonyms: allocimene, 4-trans,6-cis-; allocimene, (4E,6Z)Source: Fluka Chem. 121



100 80



E



60 40



79 41 53



20 40



105



91



136



65 60



80



100



120



140



Z



Adams: Essential Oil Components by GC/MS



200



RT: 12.72 AI: 1128 KI: 1132 Epoxy-ocimene CAS#: 33281-83-3 MF: C10 H16 O FW: 152 MSD LIB#: 1756 CN: oxirane, 2,2-dimethyl-3-[(2Z)-3-methyl-2,4-pentadienyl]Synonyms: epoxy-ocimene, myroxide Source: Wormwood cv. Powis Castle, California Gardens Nursery 79



100



O



80



Z



60 40 41 20 40



53



93



71



134



60



80



100



120



RT: 12.77 AI: 1130 KI: 1133 Terpineol CAS#: 586-82-3 MF: C10 H18 O FW: 154 CN: 1-methyl-4-(1-methylethyl)-3-cyclohexen-1-ol Synonyms: p-menth-3-en-1-ol; 3-terpinen-1-ol Source: West Indian lime oil, Lorann Oils 100



140



160



MSD LIB#: 1002



81



43



80 60 40



58



20



93



69



107



136



121



154 40



60



80



100



120



140



160



RT: 12.79 AI: 1130 KI: 1134 Cyclohexyl propanoate CAS#: 6222-35-1 MF: C9 H16 O2 FW: 156 MSD LIB#: 534 CN: propanoic acid, cyclohexyl ester Synonyms: cyclohexyl propionate Source: Bedoukian Res. ex Art Tucker 57



100



O



80



O



60 40



82



67 41



75



20 127 40



60



80



100



120



140



160



Appendix III: Mass Spectra



201



RT: 12.82 AI: 1131 KI: 1135 Linalool CAS#: 18479-51-1 MF: C10 H20 O FW: 156 MSD LIB#: 1015 CN: 6-octen-3-ol, 3,7-dimethylSynonyms: dihydrolinalool Source: SCM Chem. ex E. von Rudloff; 1.50% Citrus sinensis, JEOR 7:105(1995); 0.59% Amomum subulatum; 0.10% Eucalyptus globulus 109



100 41 69



80 60



55



40 81



20 40



60



138 123



95



80



100



120



140



160



RT: 12.82 AI: 1131 KI: 1135 Myroxide CAS#: 94607-48-4 MF: C10 H16 O FW: 152 MSD LIB#: 1119 CN: oxirane, 2,2-dimethyl-3-(3-methyl-2,4-pentadienyl)-,(Z)Synonyms: ocimene epoxide, βSource: Firmenich ex Jian-Qin Cu, Kunming 79



100 80 60 40 41 53



20 40



93



71 60



80



100



120



140



160



RT: 12.88 AI: 1132 KI: 1136 Limonene oxide (Me vs. IPP) CAS#: 13837-75-7 MF: C10 H16 O FW: 152 MSD LIB#: 1007 CN: 7-oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-,(1α,4α,6α)Synonyms: p-menth-8-ene,1,2-epoxy-,cis-; 1,2-epoxydipentene Source: Aldrich Chem. 100



43



O



80 60



67



40



79



55



20 40



109



93



137 123



60



80



100



120



152 140



160



Adams: Essential Oil Components by GC/MS



202



RT: 12.90 AI: 1133 KI: 1137 Pyrazine CAS#: 13925-06-9 MF: C9 H14 N2 FW: 150 MSD LIB#: 1353 CN: pyrazine, 2-methyl-3-(2-methylpropyl)Synonyms: none Source: Pyrazine Specialties ex Art Tucker 108



100



N



80 60



N



40 20 41



67



53



40



60



135 80



100



120



150



140



160



RT: 12.93 AI: 1133 KI: 1137 Mentha-2,8-dien-1-ol CAS#: 3886-78-0 MF: C10 H16 O FW: 152 MSD LIB#: 1070 CN: 2-cyclohexen-1-ol, 1-methyl-4-(1-methylethenyl)-, cisSynonyms: none Source: ref. cpd. ex Guy Collin 100



43



OH



80



109 79



60 40



91



67



55



20



134 119 152



40



60



80



100



120



140



160



RT: 12.94 AI: 1134 KI: 1138 Benzeneacetonitrile CAS#: 140-29-4 MF: C8 H7 N FW: 117 MSD LIB#: 1797 CN: benzeneacetonitrile Synonyms: phenylacetonitrile, benzyl cyanide, α-tolunitrile Source: Mace oil ex Mario Tellez 117



100



N



80 60



90



40 51



20 40



63 60



77 80



100



120



140



Appendix III: Mass Spectra



203



RT: 12.94 AI: 1134 KI: 1138 Thujanol CAS#: 7712-79-0 MF: C10 H18 O FW: 154 MSD LIB#: 1488 CN: bicyclo(3.1.0)hexan-3-ol, 4-methyl-1-(1-methylethyl)-,(1S-(1α,3α,4β,5α))Synonyms: isothujol, 3-thujanol (old name), new name based on menthol series nomenclature Source: ref. cpd. ex E. von Rudloff 100



43



80 55



60



H



93



40



81



67



121 107



20 40



60



OH



80



100



136 120



140



160



RT: 12.97 AI: 1134 KI: 1138 Terpineol CAS#: 3901-93-7 MF: C10 H20 O FW: 156 MSD LIB#: 1470 CN: cyclohexanol, 1-methyl-4-(1-methylethyl)-, transSynonyms: p-menthan-1-ol, transSource: SCM Chems. ex H Hills 71



100 80 60



OH



43



40 58



20 40



60



98



81 80



123



100



120



141



156



140



160



RT: 12.98 AI: 1134 KI: 1139 Cresol acetate CAS#: 533-18-6 MF: C9 H10 O2 FW: 150 MSD LIB#: 482 CN: acetic acid, 2-methylphenyl ester Synonyms: 2-acetoxytoluene; 2-methylphenyl acetate; o-tolyl acetate Source: acetylation of o-cresol(6446) 108



100 80 60



43



40 20



77



51 40



60



80



150



90 100



120



140



160



Adams: Essential Oil Components by GC/MS



204



RT: 12.99 AI: 1135 KI: 1139 Pinocarveol CAS#: 547-61-5 MF: C10 H16 O FW: 152 MSD LIB#: 1309 CN: bicyclo(3.1.1)heptan-3-ol, 6,6-dimethyl-2-methylene-, (1S-(1α,3α,5α))Synonyms: 2(10)-pinen-3-ol, (1S,3R,5S)Source: ref. cpd. ex E. von Rudloff; 26.70% Chenopodium ambrosioides, JEOR 7:221(1995); 7.50% Lavandula dentata; 7.00% Eucalyptus kirtoniana 100



41



55



92



80



70



60



OH



83



40 109



20 40



60



80



100



119



120



134 140



160



RT: 13.02 AI: 1135 KI: 1140 Nopinone CAS#: 38651-65-9 MF: C9 H14 O FW: 138 MSD LIB#: 1173 CN: bicyclo(3.1.1)heptan-2-one, 6,6-dimethylSynonyms: none Source: Aldrich Chem.; 0.08% Hyssopus officinalis, JEOR 7:39(1995); 0.03% Santolina chamaecyparissus; 0.01% Pinus pinaster 83



100 80 60



55



O



41 95



67



40



109



20 40



60



80



100



123



138



120



140



RT: 13.04 AI: 1136 KI: 1140 Menth-2-en-1-ol CAS#: 29803-81-4 MF: C10 H18 O FW: 154 MSD LIB#: 1057 CN: 2-cyclohexen-1-ol, 1-methyl-4-(1-methylethyl)-, transSynonyms: none Source: distilled from Marjoram leaves (Schilling), RP Adams #5425; 22.80% Cymbopogon jwarancusa, p. 317, in: Flav. & Frag.: A World Persp., Lawrence, etal., Proc. 10th Intl. Cong. of Ess. Oils, Elsevier, Amsterdam(1988); 1.70% Zingiber cassumunar; 1.10% Artemisia moorcroftiana 100



43



80 60 40



69



55



20



83



139



93



111



121 154



40



60



80



100



120



140



160



Appendix III: Mass Spectra



205



RT: 13.07 AI: 1137 KI: 1141 Verbenol CAS#: 1845-30-3 MF: C10 H16 O FW: 152 MSD LIB#: 1551 CN: bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1α,2β,5α)Synonyms: 2-pinen-4-ol, cisSource: ref. cpd. ex Rocky Mountain Forest Service Station, Ft. Collins, CO; 1.35% Cleonia lusitanica, JEOR 3:441(1991); 0.80% Lavandula viridis; 0.30% Juniperus flaccida 100



41 94



80



59



60



OH



109



79 67



40



119 137



20



150 40



60



80



100



120



140



160



RT: 13.08 AI: 1137 KI: 1141 Butanoate CAS#: 84254-80-8 MF: C10 H18 O2 FW: 170 MSD LIB#: 1579 CN: butanoic acid, 2-methyl-, 3-methyl-2-butenyl ester Synonyms: Source: Lomatium dasycarpum ex Vasu Dev 69



100



O



80 41



O



60 40



57



20



85 40



60



80



170 100



120



140



160



180



RT: 13.10 AI: 1137 KI: 1142 Epoxy-ocimene CAS#: 28977-57-3 MF: C10 H16 O FW: 152 MSD LIB#: 1757 CN: oxirane, 2,2-dimethyl-3-[(2E)-3-methyl-2,4-pentadienyl]Synonyms: epoxy-ocimene Source: Wormwood cv. Powis Castle ex California Gardens Nursery 79



100



O



80 60



E



43



40



91



53



20 40



67 60



109 80



100



134 120



152 140



160



Adams: Essential Oil Components by GC/MS



206



RT: 13.10 AI: 1137 KI: 1142 Limonene oxide (Me vs. IPP) CAS#: 4959-35-7 MF: C10 H16 O FW: 152 MSD LIB#: 1008 CN: 7-oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-, (1α,4β,6α)Synonyms: 1,2-epoxy-trans-p-menth-3-ene Source: Aldrich Chem. 100



43



O



80 60



67



40



94



79



108



55



20



137 40



60



80



100



120



152



140



160



RT: 13.10 AI: 1137 KI: 1142 Sabinol (trans for OH vs. IPP) CAS#: 471-16-9 MF: C10 H16 O FW: 152 MSD LIB#: 1367 CN: bicyclo(3.1.0)hexan-3-ol, 4-methylene-1-(1-methylethyl)-, (1S,3R,5S)Synonyms: 4(10)-thujen-3-ol, cis- [(-) trans-sabinol, 29606-76-6, shown] Source: ref. cpd. ex P. Weyerstahl; 14.73% Artemisia kawakamii, p. 279, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 7.00% Artemisia persica; 3.21% Artemisia absinthum 92



100 80 41



H



81



60 55



40



109



67



20 40



60



80



100



119



134



120



140



160



RT: 13.15 AI: 1138 KI: 1143 Geijerene CAS#: 6902-73-4 MF: C12 H18 FW: 162 MSD LIB#: 149 CN: cyclohexene, 4-ethenyl-4-methyl-3-(1-methylethenyl)-,(3S-trans-)Synonyms: o-mentha-3,8-diene, 1-vinyl-(1S,2S)Source: Amyris diatrypa Dom. Rep. ex Tom Zanoni; 14.60% Wiedemannia orientalis, JEOR 8:543(1996); 5.00% Skimmia laureola; 3.62% Pimpinella anisum 79



100 80 60



94



40 20 41 40



53



65 60



105 80



100



147



133 120



140



162 160



180



OH



Appendix III: Mass Spectra



207



RT: 13.18 AI: 1139 KI: 1143 Pinene hydrate CAS#: 4948-28-1 MF: C10 H18 O FW: 154 MSD LIB#: 1301 CN: bicyclo(3.1.1)heptan-2-ol, 2,6,6-trimethyl-,(1α,2α,5α)Synonyms: pinan-2-ol,cis Source: ref. cpd. ex E. von Rudloff 43



100



OH



80 93



60



71



40



55



99



81



20



111 40



60



80



100



121 136 120



140



160



RT: 13.19 AI: 1139 KI: 1144 Tagetone CAS#: 6752-80-3 MF: C10 H16 O FW: 152 MSD LIB#: 1456 CN: 5,7-octadien-4-one, 2,6-dimethyl-, (E)Synonyms: trans-tagetone Source: Tagetes minuta oil ex E. Hethelyi, Hungary 40.29% Tagetes riojana, JEOR 7:319(1995); 25.40% Tagetes tenufolia; 16.10% Tagetes lemmonii 95



100 80 67



60 40



41



20



109 60



80



100



137 120



140



152 160



RT: 13.20 AI: 1140 KI: 1144 Ocimene CAS#: 3016-19-1 MF: C10 H16 FW: 136 MSD LIB#: 1198 CN: 2,4,6-octatriene, 2,6-dimethyl-, (E,E)Synonyms: allocimene B; allocimene,(4E,6E)Source: Fluka Chem. 121



100



E



80 60



79



40 41 53



20 40



105



91



136



65 60



80



100



120



140



E



Adams: Essential Oil Components by GC/MS



208



RT: 13.20 AI: 1140 KI: 1144 Terpineol CAS#: 7299-41-4 MF: C10 H18 O FW: 154 MSD LIB#: 1003 CN: cyclohexanol, 1-methyl-4-(1-methylethenyl)-, cisSynonyms: none Source: West Indian lime oil, Lorann Oils; 6.98% Citrus paradisi, JEOR 7:105(1995); 0.90% Vitex agnus-castus; 0.85% Majorana hortensis 100



43 OH



71



80



93



60 40



55



107



84



121



136



20 40



60



80



100



120



RT: 13.21 AI: 1140 KI: 1144 Isocitral CAS#: 55050-40-3 MF: C10 H16 O FW: 152 CN: 6-octenal, 7-methyl-3-methyleneSynonyms: none Source: Backhousia citriodora oil ex. Ian Southwell 100



140



160



MSD LIB#: 1726



41



80



69



O



60 40



53 81



20 40



60



109



91



80



100



120



140



160



RT: 13.22 AI: 1140 KI: 1144 Verbenol CAS#: 1820-09-3 MF: C10 H16 O FW: 152 MSD LIB#: 1539 CN: bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1α,2α,5α)Synonyms: 2-pinen-4-ol, transSource: ref. cpd. ex Rocky Mountain Forest Service Station, Ft. Collins, CO; 7.60% Artemisia verlotiorum, FFJ 10:25(1995); 7.00% Artemisia vulgaris; 2.74% Micromeria carminea 100



109 41



OH



80



81



60



55



67



94



40



119



20



137 152



40



60



80



100



120



140



160



Appendix III: Mass Spectra



209



RT: 13.23 AI: 1140 KI: 1145 Ipsdienol CAS#: 35628-00-3 MF: C10 H16 O FW: 152 CN: 2,7-octadien-4-ol, 2-methyl-6-methyleneSynonyms: none Source: ref. cpd. ex H. Hills



MSD LIB#: 848



85



100 80 60



41



40 20



67



55 40



134 60



80



100



120



152 140



160



RT: 13.23 AI: 1140 KI: 1145 Isophorone CAS#: 1125-21-9 MF: C9 H12 O2 FW: 152 MSD LIB#: 969 CN: 2-cyclohexene-1,4-dione, 2,6,6-trimethylSynonyms: ketoisophorone; oxophorone; oxopholone Source: ref. cpd. ex Z. Fleisher 68



100



O



80



96



60



O



40 20



152



41



109



53 40



60



80



100



137 120



140



160



RT: 13.23 AI: 1140 KI: 1145 Myroxide CAS#: 28977-57-3 MF: C10 H16 O FW: 152 MSD LIB#: 1120 CN: oxirane, 2,2-dimethyl-3-(3-methyl-2,4-pentadienyl)-,(E)Synonyms: ocimene epoxide, (E)-βSource: Firmenich ex Jian-Qin Cu, Kunming 79



100 80 60 40 41 53



20



93



152



134 40



60



80



100



120



140



160



Adams: Essential Oil Components by GC/MS



210



RT: 13.28 AI: 1141 KI: 1146 Camphor CAS#: 76-22-2 MF: C10 H16 O FW: 152 MSD LIB#: 896 CN: trimethylbicyclo(2.2.1)heptan-2-one Synonyms: bornanone, 2Source: Juniperus bermudiana ex RP Adams #2554; common in conifers; 86.66% Cinnamomum parthenoxylum, p.31, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 83.87% Cinnamomum camphora; 53.46% Ocimum canum 95



100 41 81



80 60



55



69



O



108



40



152



20



137 40



60



80



100



120



140



160



RT: 13.28 AI: 1141 KI: 1146 Veratrole CAS#: 91-16-7 MF: C8 H10 O2 FW: 138 MSD LIB#: 1538 CN: benzene, 1,2-dimethoxySynonyms: catechol dimethyl ether; o-methoxyanisole; pyrocatechol dimethyl ether Source: ref. cpd. ex E. von Rudloff 138



100 80



95



77



60 40 41



123



52



65



20 40



60



80



100



120



140



RT: 13.30 AI: 1142 KI: 1146 Hexenyl isobutanoate CAS#: 41519-23-7 MF: C10 H18 O2 FW: 170 MSD LIB#: 811 CN: propanoic acid, 2-methyl-, 3-hexenyl ester, (Z)Synonyms: hexenyl isobutyrate Source: ref. cpd. ex Art Tucker 100



67



43



80



O



O



82



60 40 55



20 40



60



80



100



120



140



160



180



Z



Appendix III: Mass Spectra



211



RT: 13.33 AI: 1143 KI: 1147 Terpineol CAS#: 5114-00-1 MF: C10 H20 O FW: 156 MSD LIB#: 1472 CN: cyclohexanemethanol, α,α,4-trimethyl-, transSynonyms: p-menthan-8-ol, transSource: ref. cpd. ex E. von Rudloff 59



100 80 60 40 20



OH



43



81



40



60



123



80



100



120



141 140



160



RT: 13.34 AI: 1143 KI: 1147 Isoamyl angelate CAS#: 10482-55-0 MF: C10 H18 O2 FW: 170 MSD LIB#: 1989 CN: 2-butenoic acid, 2-methyl-, 3-methylbutyl ester (Z)Synonyms: none Source: Soda Aromatics ex JJ Brophy; 17.90% Anthemis nobilis (Italy), J. HRC & CC 5:182(1982); 17.38% Anthemis nobilis (England); 8.39% Anthemis nobilis (Egypt) 100



100 80



43



55



O



Z



60



83



O



71



40 20



170 40



60



80



100



120



140



160



180



RT: 13.37 AI: 1144 KI: 1148 Isopulegol CAS#: 59905-53-2 MF: C10 H18 O FW: 154 MSD LIB#: 880 CN: cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1α, 2β,5α)Synonyms: none Source: Aldrich Chem. 100



41



80



67



55



60



81



40



121



95 111



136



20



154 40



60



80



100



120



140



160



Adams: Essential Oil Components by GC/MS



212



RT: 13.37 AI: 1144 KI: 1148 Necrodol CAS#: 104104-38-3 MF: C10 H18 O FW: 154 MSD LIB#: 2094 CN: 2-cyclopentene-1-methanol, 3,4,5,5-tetramethyl-, (1R-trans-) Synonyms: none Source: Lavandula luisieri, ex Nicolas Baldovini 123



100



OH



80 81



60 40 41 20 40



55



139 91



67 60



80



154



107 100



120



140



160



RT: 13.38 AI: 1144 KI: 1148 Heptalactone CAS#: 105-21-5 MF: C7 H12 O2 FW: 128 MSD LIB#: 1915 CN: 2(3H)-furanone, dihydro-5-propylSynonyms: 4-heptanolide Source: ref. cpd. ex JJ Brophy; 0.15% Zizyphus jujuba (fruit), JEOR 8:323-326(1996); 0.04% Citrus bergamia



O



O



RT: 13.40 AI: 1144 KI: 1149 Nonen-1-al CAS#: 60784-31-8 MF: C9 H16 O FW: 140 MSD LIB#: 1169 CN: 2-nonenal, (Z)Synonyms: none Source: Bedoukian Res. ex Art Tucker; 0.24% Micromeria carminea, JEOR 7:457(1995); 0.11% Sideritis dichotoma; 0.01% Pistacia vera (fruit hull) 100



41



80



H



Z



55



O



70



60



83



40 20



96 40



60



80



100



120



140



Appendix III: Mass Spectra



213



RT: 13.43 AI: 1145 KI: 1149 Camphene hydrate CAS#: 64474-11-9 MF: C10 H18 O FW: 154 MSD LIB#: 904 CN: bicyclo(2.2.1)heptan-2-ol, 2,3,3-trimethyl-,(1R-endo)Synonyms: 3-methylcamphenilanol; 3-methylcamphenilol Source: Juniperus flaccida var. poblana ex RP Adams #2578; common in conifers; 2.31% Artemisia annua (leaf), JEOR 3:33 (1991); 2.10% Curcuma aromatica; 2.09% Artemisia annua (flower) 100



43 71



80



OH



60 40



86



55



20 40



60



96



80



111



100



121 120



136



154



140



160



RT: 13.43 AI: 1145 KI: 1149 Isopulegol CAS#: 121468-66-4 MF: C10 H18 O FW: 154 MSD LIB#: 879 CN: cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1α,2α,5β)Synonyms: none Source: Aldrich Chem.; 11.20% Satureja gilliesii, JEOR 8:183(1996); 10.33% Eucalyptus citriodora; 4.90% Citrus hystrix 100



41



80



67



55



60



81



121



93



40



111



136



20



154 40



60



80



100



120



140



160



RT: 13.43 AI: 1145 KI: 1149 Myrcenone CAS#: 539-70-8 MF: C10 H14 O FW: 150 MSD LIB#: 1020 CN: 2,7-octadien-4-one, 2-methyl-6-methyleneSynonyms: ipsdienone Source: Lippia javanica oil ex JW Mwangi, Kenya; 14.85% Hyptis mutabilis, JEOR 7:81(1995) 83



100 80 60



55



40



O



20 41 40



150 60



80



100



120



140



160



Adams: Essential Oil Components by GC/MS



214



RT: 13.45 AI: 1145 KI: 1150 Menth-3-en-8-ol CAS#: 24302-23-6 MF: C10 H18 O FW: 154 MSD LIB#: 588 CN: 1-cyclohexene-1-methanol, α,α,4-trimethylSynonyms: p-menth-3-en-8-ol Source: Dicerandra frutescens oil ex Mark Deyrup, FL 100



43



80 60 139



40



59



20



67 40



60



81



121



95



80



100



120



154 140



160



RT: 13.47 AI: 1146 KI: 1150 Eucarvone CAS#: 503-93-5 MF: C10 H14 O FW: 150 MSD LIB#: 1793 CN: 2,4-cycloheptadien-1-one, 2,6,6-trimethylSynonyms: none Source: ref. cpd. ex Ian Southwell; 1.70% Melissa officinalis, in: Flavour Composition of Lemon Balm, I. Nykaenen, etal., Lebensm.-Wisc. U-Technol., 19:482(1986); 0.40% Angelica archangelica; 0.36% Ribes nigrum 107



100 80 60 40



91 41



40



150



65



53



20



O



79



60



122 80



100



120



135 140



160



RT: 13.47 AI: 1146 KI: 1150 Phenol CAS#: 23508-99-8 MF: C9 H10 O FW: 134 MSD LIB#: 1271 CN: phenol, 2-(1Z)-1-propenylSynonyms: none Source: Aldrich Chem. 134



100



Z



80



91



OH



60



119



77



51



40



105



63



20



43 40



60



80



100



120



140



Appendix III: Mass Spectra



215



RT: 13.50 AI: 1147 KI: 1151 Hexyl isobutanoate CAS#: 2349-07-7 MF: C10 H20 O2 FW: 172 CN: propanoic acid, 2-methyl-, hexyl ester Synonyms: hexyl isobutyrate Source: Pfaltz & Bauer ex Art Tucker 100



MSD LIB#: 817



43



80 60 40



89



71



56



20 129 40



60



80



100



120



140



160



180



RT: 13.50 AI: 1147 KI: 1151 Thujanol CAS#: 21653-19-0 MF: C10 H18 O FW: 154 MSD LIB#: 1490 CN: bicyclo(3.1.0)hexan-3-ol, 4-methyl-1-(1-methylethyl)-, (1S-(1α,3β,4β,5α))Synonyms: neoisothujol Source: ref. cpd. ex E. von Rudloff 100



43 H



80 93



55



60



121



81



67



40



136



107



20 40



OH



60



80



100



120



140



160



RT: 13.51 AI: 1147 KI: 1151 Butanoate CAS#: 89026-29-9 MF: C10 H18 O2 FW: 170 MSD LIB#: 1580 CN: butanoic acid, 3-methyl-, 3-methyl-2-butenyl ester Synonyms: 3-methyl-2-butenyl isovalerate Source: Lomatium dasycarpum ex Vasu Dev 100



41



O



69



80



O



60



57



40



85



20 170



128 40



60



80



100



120



140



160



180



Adams: Essential Oil Components by GC/MS



216



RT: 13.54 AI: 1148 KI: 1152 Tagetone CAS#: 3588-18-9 MF: C10 H16 O FW: 152 MSD LIB#: 1455 CN: 5,7-octadien-4-one, 2,6-dimethyl-, (Z)Synonyms: cis-tagetone Source: Tagetes minuta oil ex E. Hethelyi, Hungary; 68.20% Tagetes terniflora, JEOR 5:679(1993); 27.15% Tagetes minuta; 11.00% Lippia dauensis 95



100 80



67



60 41 40



109



20



152 137



53 60



80



100



120



140



160



RT: 13.55 AI: 1148 KI: 1152 Menthone CAS#: 89-80-5 MF: C10 H18 O FW: 154 MSD LIB#: 1261 CN: cyclohexanone, 5-methyl-2-(1-methylethyl)-, transSynonyms: p-menthan-3-one, transSource: Peppermint oil, McCormick Co.; 60.00% Mentha longifolia, Parf., Cosm., Aromes 64:83(1985); 57.20% Mentha spicata; 54.11% Satureja boliviana 112



100 41 69



80



55



60



139



40



83



97



O



154



20



125 40



60



80



100



120



140



160



RT: 13.58 AI: 1148 KI: 1153 Citronellal CAS#: 106-23-0 MF: C10 H18 O FW: 154 MSD LIB#: 923 CN: dimethyl-6-octenal Synonyms: 2,3-dihydrocitral; rhodinal;3,7-dimethyl-6-octenal Source: Juniperus monticola f. compacta leaves, RP Adams #2580; 86.22 Eucalyptus citriodora, p. 50, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 76.55% Litsea cubeba; 65.40% Citrus hystrix 100



41



80



69



60



O



95



55



40 20



111



84 40



60



80



100



121 139 120



140



154 160



Appendix III: Mass Spectra



217



RT: 13.59 AI: 1149 KI: 1153 Ethyl hexyl acetate CAS#: 103-09-3 MF: C10 H20 O2 FW: 172 MSD LIB#: 673 CN: acetic acid, 2-ethylhexyl ester Synonyms: 2-ethylhexyl ethanoate Source: Aldrich Chem.; 1.10% Alpinia katsumadai (seed), JEOR 2:259(1990); 0.10% Alpinia chinensis (flower) 100



43



O



80



O



60



70



40



57



20



83 40



60



80



100



120



140



160



180



RT: 13.59 AI: 1149 KI: 1153 Nonadienol CAS#: 56805-23-3 MF: C9 H16 O FW: 140 MSD LIB#: 2129 CN: 3,6-nonadien-1-ol, (3E,6Z)Synonyms: none Source: Bedoukian Res. 67



100 80



E



41



60



Z



HO



55



40



79



93



20



109 40



60



80



140



100



120



140



RT: 13.60 AI: 1149 KI: 1153 Thujanol CAS#: 21653-18-9 MF: C10 H18 O FW: 154 MSD LIB#: 1491 CN: bicyclo(3.1.0)hexan-3-ol, 4-methyl-1-(1-methylethyl)-, (1S-(1α,3β,4α,5α))Synonyms: neothujol Source: ref. cpd. ex E. von Rudloff; 0.26% Artemisia moorcroftiana, p.26, in: Newer Trends in Ess. Oils & Flav., P. Weyerstahl, New Delhi, India(1993) 100



43 H



80 55



60



93



40



67



81



121 107



20 40



60



80



100



136 120



140



160



OH



Adams: Essential Oil Components by GC/MS



218



RT: 13.62 AI: 1149 KI: 1154 Isobutyl hexanoate CAS#: 105-79-3 MF: C10 H20 O2 FW: 172 MSD LIB#: 1614 CN: hexanoic acid, 2-methylpropyl ester Synonyms: isobutyl caproate Source: Aldrich Chem.; 1.32% Michelia balansae, p. 15, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.23% Michelia figo (flower) 99



100



O



80



43



60



O



56



40



117



71



20



87 40



60



80



129 100



120



142 140



160



180



RT: 13.64 AI: 1150 KI: 1154 Nonadienal CAS#: 557-48-2 MF: C9 H14 O FW: 138 MSD LIB#: 1162 CN: 2,6-nonadienal, (E,Z)Synonyms: cucumber aldehyde; nonadienal, trans-2,cis-6-; violet leaf aldehyde Source: Aldrich Chem. ex Art Tucker; 13.00% Viola odorata, Phytochemistry 31:571(1992); 0.10% Narcissus poeticus; 0.07% Acacia farnesiana 100



41



H



Z



E



80



O



60



70



40 20



53 40



60



80



100



120



140



RT: 13.73 AI: 1152 KI: 1156 Benzene CAS#: 538-68-1 MF: C11 H16 FW: 148 MSD LIB#: 422 CN: benzene, pentylSynonyms: amylbenzene; phenylpentane; pentylbenzene Source: Celery seed oil (distilled in lab), RP Adams #5434 91



100 80 60 40 20 41 40



65



51 60



148 105



78 80



100



133 120



140



Appendix III: Mass Spectra



219



RT: 13.74 AI: 1152 KI: 1157 Nonen-1-ol CAS#: 10340-23-5 MF: C9 H18 O FW: 142 MSD LIB#: 1170 CN: 3-nonen-1-ol, (Z)Synonyms: none Source: Aldrich Chem.; 0.72% Acacia farnesiana (blossom absolute), J. Ag. Food Chem. 31:1167(1983) 100



41



Z



HO



55



80



68



60



81



40



95



20 40



60



80



100



120



140



RT: 13.79 AI: 1153 KI: 1158 Phenyl-tert-butanol CAS#: 100-86-7 MF: C10 H14 O FW: 150 MSD LIB#: 1284 CN: benzene ethanol, α, α-dimethylSynonyms: 2-benzyl-2-propanol; benzyldimethylcarbinol Source: K & K Chem. ex Art Tucker 92



100 80



59



60 40



43



20



65



51 40



60



117 80



100



120



135 140



160



RT: 13.80 AI: 1154 KI: 1158 Nerol oxide CAS#: 1786-08-9 MF: C10 H16 O FW: 152 MSD LIB#: 1139 CN: 2H-pyran, 3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)Synonyms: none Source: Firmenich ex Jian-Qin Cu, Kunming; 0.15% Zanthoxylum nitidum, p. 75, in: Newer Trends in Ess. Oils & Flav., P. Weyerstahl, New Delhi, India(1993); 0.10% Dracocephalum moldavica; 0.09% Rosa damascena 68



100 80



83



60 41 40



53



20



96 40



60



80



100



137 120



140



152 160



Adams: Essential Oil Components by GC/MS



220



RT: 13.82 AI: 1154 KI: 1159 Karahanaenone CAS#: 19822-67-4 MF: C10 H16 O FW: 152 MSD LIB#: 516 CN: 4-cyclohepten-1-one, 2,2,5-trimethylSynonyms: none Source: Cupressus sargentii oil ex Larry Cool; 0.70% Cupressus sempervirens, in: Contribution to the study of the chemical composition of cypress oil, J. Garnero, etal, Paper #112, Cong. Ess. Oils, Kyoto(1977) 100



41 67



80



95



81



60



152 109



53



40 20



119 40



60



80



100



120



137 140



160



RT: 13.83 AI: 1154 KI: 1159 Pinene oxide CAS#: 6931-54-0 MF: C10 H16 O FW: 152 MSD LIB#: 1303 CN: spiro(bicyclo(3.1.1)heptane-2,2'-oxirane), 6,6-dimethylSynonyms: pinane, 2,10-epoxySource: Aldrich Chem. ex H. Hills; 0.20% Juniperus foetidissima (leaf), JEOR 2:67(1990); 0.20% Juniperus martinezii 100



41



80



79



67



60



55



40



109



91



123 137



20



152 40



60



80



100



120



140



160



RT: 13.83 AI: 1154 KI: 1159 Sabina ketone CAS#: 513-20-2 MF: C9 H14 O FW: 138 MSD LIB#: 212 CN: bicyclo(3.1.0)hexan-2-one, 5-(1-methylethyl)Synonyms: none Source: Artemisia persica oil ex P. Weyerstahl; 3.00% Artemisia roxburghiana, JEOR 6:345(1994); 1.70% Artemisia persica; 1.53% Artemisia gmelini 81



100 80 41



55



67



60



95



40 20



109 40



60



80



100



123 120



138 140



Appendix III: Mass Spectra



221



RT: 13.86 AI: 1155 KI: 1159 Isopulegol CAS#: 59905-54-3 MF: C10 H18 O FW: 154 MSD LIB#: 878 CN: cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1α,2β,5β)Synonyms: none Source: Aldrich Chem. 100



41



80



67



55



60 40



121



95



81



111



OH



136



20



154 40



60



80



100



120



140



160



RT: 13.87 AI: 1155 KI: 1160 Hydroxy acetophenone CAS#: 586-37-8 MF: C9 H10 O2 FW: 150 MSD LIB#: 11 CN: ethanone, 1-(3-methoxyphenyl)Synonyms: acetanisole, metaSource: Aldrich Chem. 135



100



O-Me



80 77



60 40



107



43



20 40



92



64



50



150



60



80



Ac



100



120



140



160



RT: 20.11 AI: 1298 KI: 1298 Azulene CAS#: 275-51-4 MF: C10 H8 FW: 128 MSD LIB#: 262 CN: cyclopentacycloheptene Synonyms: none Source: Aldrich Chem. ex H. Hills; 2.75% Dendrobium chrysatoxum (flower), p. 111, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.97% Artemisia macrocephala; 0.45% Michelia yunnanesis (flower) 128



100 80 60 40 20



51 40



63 60



102



74 80



100



120



140



Appendix III: Mass Spectra



335



RT: 20.11 AI: 1298 KI: 1298 Geranyl formate CAS#: 105-86-2 MF: C11 H18 O2 FW: 182 MSD LIB#: 732 CN: 2,6-octadien-1-ol, 3,7-dimethyl-, formate, (E)Synonyms: geraniol formate Source: Firmenich ex AF Thomas; 9.65% Pelargonium graveolens, JEOR 2:73(1990); 5.00% Cymbopogon martini; 4.20% Cymbopogon nardus 69



100 80 41 60 40 20



93



53 40



60



80



121 100



136



120



140



160



180



200



RT: 20.11 AI: 1298 KI: 1298 Pinocarvyl acetate CAS#: 1686-15-3 MF: C12 H18 O2 FW: 194 MSD LIB#: 1311 CN: bicyclo(3.1.1)heptan-3-ol, 6,6-dimethyl-2-methylene-, acetate,(1α,3α,5α)Synonyms: 2(10)-pinen-3-ol, acetate, transSource: ref. cpd. ex E. von Rudloff; 49.00% Egletes viscosa, JEOR 4:639(1992); 1.00% Eucalyptus botryoides; 0.24% Acorus calamus 100



43



80 60



91



O-Ac



40 20



53 40



69 60



119 79



108



80



100



134 120



152



140



160



180



200



RT: 20.12 AI: 1298 KI: 1298 Carquejol acetate CAS#: 32151-09-0 MF: C12 H16 O2 FW: 192 MSD LIB#: 1290 CN: 2-cyclohexen-1-ol, 5-methylene-6-(1-methylethenyl)-, acetate,(1S-cis)Synonyms: o-mentha-1(7),4,8-trien-3-ol, acetate (2R,3S)Source: Phoebe oil ex P. Weyerstahl; 42.82% Baccharis porosa, FFJ 9:179(1994); 2.10% Phoebe porosa 100



43



O-Ac



80 60



117



40



91



20



65



53 40



60



132



79 80



107 100



150 120



140



160



180



200



Adams: Essential Oil Components by GC/MS



336



RT: 20.13 AI: 1298 KI: 1298 Octenol propanoate CAS#: 196109-18-9 MF: C11 H20 O2 FW: 184 MSD LIB#: 2056 CN: 5-octen-1-ol, propanoate, (5Z)Synonyms: none Source: Bedoukian Res. O



82



100



57



67



Z



80 60 41 40



O



110 95



20 40



60



80



100



120



140



160



180



200



RT: 20.14 AI: 1298 KI: 1299 Carvacrol CAS#: 499-75-2 MF: C10 H14 O FW: 150 MSD LIB#: 1507 CN: 2-methyl-5-(1-methylethyl) phenol Synonyms: p-cymen-2-ol; antioxine, isothymol; 2-hydroxy-ρ-cymene, isopropyl-ο-cresol Source: distilled from Thyme leaves, RP Adams #5426 ex Schilling; Oreganum; Marjoram; 86.33% Coridothymus capitatus, JEOR 4:417(1992); 78.85% Majorana hortensis; 71.40% Thymbra spicata 135



100 80 60 40 20



150 41



91



77



51 60



80



107 115 100



120



140



160



RT: 20.17 AI: 1299 KI: 1299 Terpinen-4-ol acetate CAS#: 4821-04-9 MF: C12 H20 O2 FW: 196 MSD LIB#: 1560 CN: 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, acetate Synonyms: p-menth-1-en-4-ol acetate Source: Cupressus lusitanica oil, Portugal, RP Adams #7123 100



43



93



80 60



121



40 53



20



67



136



O-Ac



111



77



165 40



60



80



100



120



140



160



180



200



Appendix III: Mass Spectra



337



RT: 20.18 AI: 1299 KI: 1299 Methyl cinnamate CAS#: 19713-73-6 MF: C10 H10 O2 FW: 162 MSD LIB#: 266 CN: 2-propenoic acid, 3-phenyl-, methyl ester, (Z)Synonyms: cis-cinnamic acid, methyl ester Source: distillation of basil leaves ex McCormick Co., RP Adams #5435; 9.40% Ocimum basilicum, FFJ 1:53(1986); 0.78% Ocimum basilicum (CO2-extract); 0.41% Artemisia judaica 131



100 80



103



60



162



77



40



Z



51



20 40



O-Me



91



63 60



O



144



80



100



120



140



160



180



RT: 20.18 AI: 1299 KI: 1299 Necrodol acetate CAS#: 709026-15-3 MF: C12 H20 O2 FW: 196 MSD LIB#: 2097 CN: 2-cyclopentene-1-methanol, 3,4,5,5-tetramethyl-, acetate, cisSynonyms: none Source: Lavandula luisieri, ex Nicolas Baldovini 121



100



O-Ac



80 60 40



43



20



55 40



67 60



136



81



91



80



105 100



120



140



160



180



200



RT: 20.18 AI: 1299 KI: 1299 Undec-10-en-1-al CAS#: 112-45-8 MF: C11 H20 O FW: 168 MSD LIB#: 1519 CN: 10-undecenal Synonyms: none Source: Givaudan ex Jian-Qin Cu, Kunming; 0.10% Coriandrum sativum, J. Ag. Food Chem. 38:2054(1990) 100



41 55



80 60



67



40



82



20 40



60



80



98 100



111 121 120



135 140



160



180



Adams: Essential Oil Components by GC/MS



338



RT: 20.19 AI: 1300 KI: 1300 Tridecane CAS#: 629-50-5 MF: C13 H28 FW: 184 MSD LIB#: 93 CN: tridecane Synonyms: none Source: Alltech Assoc.; 0.70% Brassica juncea (flower), Nippon Nogeikagaku Kaishi 54:99(1980); 0.50% Hypericum perforatum; 0.50% Brassica juncea (leaves & stem) 100



57



43



80 71



60 40



85



20



99 40



60



80



127



100



141



120



140



RT: 20.20 AI: 1300 KI: 1300 Undecenal CAS#: 147159-49-7 MF: C11 H20 O FW: 168 CN: 8-undecenal, (8Z)Synonyms: none Source: Bedoukian Res. 100



184



155 160



180



200



MSD LIB#: 2133



41



O



Z



80



55



60 40



67



20 40



60



82 80



98



111



100



121 120



135



150



140



160



180



RT: 20.22 AI: 1300 KI: 1300 Terpinyl acetate CAS#: 20777-41-7 MF: C12 H22 O2 FW: 198 MSD LIB#: 1468 CN: cyclohexanemethanol, α,α,4-trimethyl-, acetate, transSynonyms: p-menthan-8-ol acetate, transSource: acetylation of cis-dihydro-α-terpineol(6269) 100



43



80 60 O-Ac



40



55 67



20 60



81



80



95101 100



123 138 131 120



140



160



180



200



220



240



Appendix III: Mass Spectra



339



RT: 20.26 AI: 1301 KI: 1301 Undecanol CAS#: 1653-30-1 MF: C11 H24 O FW: 172 MSD LIB#: 1818 CN: 2-undecanol Synonyms: sec-undecyl alcohol Source: alcohols mix (2-OHs) ex K-H Kubeczka; 0.80% Ruta graveolens, Sci. Pharm. 56:121(1988); 0.51% Rosa rugosa; 0.30% Curcuma aeruginosa 45



100



(CH2)8-CH3



80



OH



60 40 55



20 40



69 60



83



140



80



100



120



140



160



180



RT: 20.29 AI: 1302 KI: 1302 Elsholtzia ketone CAS#: 6138-88-1 MF: C10 H12 O2 FW: 164 MSD LIB#: 656 CN: 2-buten-1-one, 3-methyl-1-(3-methyl-2-furanyl)Synonyms: naginata ketone; elsholtzione, dehydroSource: Elsholtzia cristata ex O. Vostrowsky, Planta Med. 3:268(1987) 100



93



121



80



147



109



60



164



136



O



53



40



77



O



67



20 41 40



60



80



100



120



140



160



180



RT: 20.29 AI: 1302 KI: 1302 Vanillin CAS#: 148-53-8 MF: C8 H8 O3 FW: 152 MSD LIB#: 1193 CN: benzaldehyde, 2-hydroxy-3-methoxySynonyms: m-anisaldehyde, 2-hydroxy-; 6-formylguaiacol Source: Pfaltz & Bauer ex H Hills 152



100 80 60



106



40



81



53



20



63 40



60



122



92 80



100



120



136 140



160



Adams: Essential Oil Components by GC/MS



340



RT: 20.36 AI: 1303 KI: 1304 Cinnamyl alcohol CAS#: 4407-36-7 MF: C9 H10 O FW: 134 MSD LIB#: 449 CN: 2-propen-1-ol, 3-phenyl-, (E)Synonyms: trans-cinnamyl alcohol Source: Aldrich Chem. ex H. Hills 92



100 80



78



60



105



51



40



134 115



E



63



20



OH



40



60



80



100



120



140



RT: 20.36 AI: 1303 KI: 1304 Nonadienol acetate CAS#: 68555-65-7 MF: C11 H18 O2 FW: 182 MSD LIB#: 2127 CN: 2,6-nonadien-1-ol,acetate (E,Z)Synonyms: none Source: Bedoukian Res. 100



43



E



Z



O-Ac



80 60 40 68



54



20 40



60



79



93



80



122 100



120



140



160



180



RT: 20.39 AI: 1304 KI: 1305 Menthyl acetate CAS#: 20777-45-1 MF: C12 H22 O2 FW: 198 MSD LIB#: 1263 CN: cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate,(1α,2β,5β)Synonyms: none Source: Acetylation of peppermint oil (5498) 100



43 95



80 60



O-Ac



81



40



55



20 40



123



67 60



138



109 80



100



158 120



140



160



180



200



Appendix III: Mass Spectra



341



RT: 20.40 AI: 1304 KI: 1305 Butanoic acid, 2-methyl-4-methylhexyl ester CAS#: 850309-46-5 MF: C12 H24 O2 FW: 200 MSD LIB#: 2163 CN: butanoic acid, 2-methyl, 4-methylhexyl ester Synonyms: none Source: Lomatium dissectum root oil ex Vasu Dev 57



100 80 60



O



O



41 103



70



40



85



20



143 40



60



80



100



120



140



172 160



180



200



RT: 20.42 AI: 1305 KI: 1305 Cresyl isobutyrate CAS#: 103-93-5 MF: C11 H14 O2 FW: 178 MSD LIB#: 2181 CN: propanoic acid, 2-methyl-, 4-methylphenyl ester Synonyms: tolyl isobutyrate, p-; Source: Bedoukian Res. 108



100 80 60



43



40 20



71



51



77



178



O



O



40



60



80



100



120



140



160



180



RT: 20.45 AI: 1305 KI: 1306 Undecanal CAS#: 112-44-7 MF: C11 H22 O FW: 170 MSD LIB#: 1523 CN: undecanal Synonyms: hendecanal Source: Aldrich Chem. ex Art Tucker; 5.00% Machilus bombycina, JEOR 7:199(1995); 3.04% Coriandrum sativum; 2.08% Narcissus tazetta 100



41



80



57



60 40



68



82 95



20 40



60



80



100



109



126 120



142 152 140



160



180



Adams: Essential Oil Components by GC/MS



342



RT: 20.48 AI: 1306 KI: 1307 Dihydro carveol acetate CAS#: 75684-64-9 MF: C12 H20 O2 FW: 196 MSD LIB#: 596 CN: cyclohexanol, 2-methyl-5-(1-methylethenyl)-, acetate, (1R-(1α,2α,5β))Synonyms: none Source: ref. cpd., E von Rudloff 100



43



80 60



79



107



93



40



136



67



55



20



121



154 40



60



80



100



120



140



160



180



200



180



200



RT: 20.48 AI: 1306 KI: 1307 Dihydro carveol acetate CAS#: 75684-65-0 MF: C12 H20 O2 FW: 196 MSD LIB#: 597 CN: cyclohexanol, 2-methyl-5-(1-methylethenyl)-, acetate,(1α,2β,5α)Synonyms: dihydrocarvyl acetate Source: ref. cpd. ex E. von Rudloff 100



43



80 60



79



107



93



40



136



67



55



20



121



154 40



60



80



100



120



140



160



RT: 20.49 AI: 1306 KI: 1307 Nonenol acetate CAS#: 30418-89-4 MF: C11 H20 O2 FW: 184 MSD LIB#: 2083 CN: 2-nonen-1-ol, acetate, (2E)Synonyms: none Source: Bedoukian Res. 100



43



E AcO



80 60 40



54 67



20 40



60



82 80



96 100



142 120



140



160



180



200



Appendix III: Mass Spectra



343



RT: 20.58 AI: 1308 KI: 1309 Verbanol acetate CAS#: 73366-11-7 MF: C12 H20 O2 FW: 196 MSD LIB#: 1541 CN: bicyclo(3.1.1)heptan-2-ol, 4,6,6-trimethyl-, acetate,(1α,2α,4β,5α)Synonyms: none Source: acetylation of verbanols(6314) 100



43



O-Ac



80 60



93



40



121



85



55



107



67



20 40



60



80



100



136 120



154



140



160



180



200



RT: 20.59 AI: 1309 KI: 1309 Guaiacol CAS#: 7786-61-0 MF: C9 H10 O2 FW: 150 MSD LIB#: 1662 CN: 2-methoxy-4-vinylphenol Synonyms: p-vinylguaiacol, phenol Source: Aldrich Chem. 100



77



OH



135



107



150



O



80 60 40



51



63



20 40



89



60



80



100



120



140



160



RT: 20.61 AI: 1309 KI: 1310 Tetrahydro jasmone CAS#: 71535-29-0 MF: C11 H20 O FW: 168 MSD LIB#: 1956 CN: cyclopentanone, 3-methyl-2-pentyl-, transSynonyms: none Source: Bedoukian Res. ex JJ Brophy O



83



100 80 60 40



98 41



55



20



69 40



60



139 80



100



120



140



153



168 160



180



Adams: Essential Oil Components by GC/MS



344



RT: 20.63 AI: 1309 KI: 1310 Carvotanacetone CAS#: 131486-99-2 MF: C10 H16 O2 FW: 168 MSD LIB#: 974 CN: 2-cyclohexen-1-one, 6-hydroxy-2-methyl-5-(1-methylethyl)Synonyms: none Source: Laggera alata oil ex JJ Scheffer 82



100



O



80 60 40 20



OH



41



54



40



73



128



60



80



100



120



RT: 20.63 AI: 1309 KI: 1310 Veloutone CAS#: 65443-14-3 MF: C13 H24 O FW: 196 CN: cyclopentanone, 2,2,5-trimethyl-5-pentylSynonyms: none Source: Firmenich ex Jian-Qin Cu, Kunming



140



160



180



MSD LIB#: 1537



56



100 80



168



140 150



O



126



41



60 40



111



69



20



84 40



60



97



80



196



100



120



140



160



180



200



RT: 20.64 AI: 1310 KI: 1311 Adamantanone CAS#: 700-58-3 MF: C10 H14 O FW: 150 MSD LIB#: 1995 CN: tricyclo(3.3.1.13,7)decanone Synonyms: 2-oxoadamantane Source: Aldrich Chem. ex JJ Brophy 150



100 79



80 60 40



O



41



20 40



53



91



67 60



80



104 100



117 132 120



140



160



Appendix III: Mass Spectra



345



RT: 20.64 AI: 1310 KI: 1311 Isoamyl benzyl ether CAS#: 122-73-6 MF: C12 H18 O FW: 178 MSD LIB#: 851 CN: benzene, ((3-methylbutoxy)methyl)Synonyms: isopentyl benzyl ether Source: Pfaltz & Bauer ex Art Tucker 91



100 80 60 40 20 41



65



51



40



77



60



108



80



100



120



140



160



180



RT: 20.68 AI: 1311 KI: 1312 Pinocarvyl acetate CAS#: 73366-18-4 MF: C12 H18 O2 FW: 194 MSD LIB#: 1312 CN: bicyclo(3.1.1)heptan-3-ol, 6,6-dimethyl-2-methylene-, acetate,(1α,3β,5α)Synonyms: none Source: ref. cpd. ex E. von Rudloff 100



43



80 O-Ac



60



91



40 20



53 40



69 60



119 79 80



108 100



134 120



140



152 160



180



200



RT: 20.69 AI: 1311 KI: 1312 Nonanyl acetate CAS#: 143-13-5 MF: C11 H22 O2 FW: 186 MSD LIB#: 1171 CN: acetic acid, nonyl ester Synonyms: pelargonyl acetate Source: K & K Chem. ex H. Hills 100



43



80 60 40



56



20 40



60



70



83 80



97 100



126 120



140



160



180



200



Adams: Essential Oil Components by GC/MS



346



RT: 20.69 AI: 1311 KI: 1312 Sesamol CAS#: 533-31-3 MF: C7 H6 O3 FW: 138 CN: 1,3-benzodioxol-5-ol Synonyms: phenol, 3,4-(methylenedioxy)Source: ref. cpd. ex E. von Rudloff



MSD LIB#: 1405



138



100 80



52



60



69 41



80



62



40



107



60



80



100



RT: 20.70 AI: 1311 KI: 1312 Undec-(9E)-en-1-al CAS#: 143-14-6 MF: C11 H20 O FW: 168 CN: 9-undecenal Synonyms: 9-hendecenal Source: Givaudan ex Jian-Qin Cu, Kunming 100 41



120



140



MSD LIB#: 1520



55



80 60 67



40



82



20 40



60



95



80



111



100



121



150



135



120



140



160



180



RT: 20.73 AI: 1312 KI: 1313 Isopulegyl acetate CAS#: 000-00-0 MF: C12 H20 O2 FW: 196 MSD LIB#: 882 CN: not assigned Synonyms: none Source: Aldrich Chem. 100



43



80 60 40 20



67



55



79



93



107



121



136 145



40



60



O



O



40 20



HO



80



100



120



140



163 160



180



200



Appendix III: Mass Spectra



347



RT: 20.74 AI: 1312 KI: 1313 Cyclohexanol acetate CAS#: 20298-70-8 MF: C12 H22 O2 FW: 198 MSD LIB#: 542 CN: cyclohexanol, 2-(1,1-dimethylethyl)-, acetate, transSynonyms: none Source: ref. cpd. ex Art Tucker 100



57 43



80



82 67



60



O-Ac



40 20



123 40



60



80



100



138



120



140



160



180



200



RT: 20.75 AI: 1312 KI: 1313 Citronellic acid CAS#: 502-47-6 MF: C10 H18 O2 FW: 170 MSD LIB#: 1717 CN: 6-octenoic acid, 3,7-dimethylSynonyms: none Source: ref. cpd. ex E. von Rudloff; 4.70% Eucalyptus citriodora, JEOR 4:259(1992); 0.52% Citrus hystrix (twig); 0.41% Citrus paradisi (leaf) 100



41



O



80



OH



60



69



40



55



95



20



110



82 40



60



80



100



170



152 120



140



160



180



RT: 20.79 AI: 1313 KI: 1314 Trimethyl benzaldehyde CAS#: 34341-28-1 MF: C10 H12 O FW: 148 MSD LIB#: 660 CN: benzaldehyde, 2,3,4-trimethylSynonyms: none Source: Eryngium foetidum oil ex KC Wong, Malaysia 148



100



119



80 60



91



40 20



41 40



51 63 60



105



77 131 80



100



120



140



O



Adams: Essential Oil Components by GC/MS



348



RT: 20.83 AI: 1314 KI: 1315 Cryptone CAS#: 39725-34-3 MF: C9 H14 O2 FW: 154 MSD LIB#: 1421 CN: 2-cyclohexene-1-one, 4-hydroxy-4-(1-methylethyl)Synonyms: 2-cyclohexen-1-one, 4-hydroxy-4-(1-methylethyl)Source: Solidago graminifolia oil ex P. Weyerstahl 111



100 80 60



55



83



43



40 20



67 40



95



60



80



126 100



120



139 140



160



RT: 20.87 AI: 1315 KI: 1316 Decadienal CAS#: 25152-84-5 MF: C10 H16 O FW: 152 MSD LIB#: 564 CN: 2,4-decadienal, (E,E)Synonyms: 2-trans, 4-trans-decadienal Source: ref. cpd. ex Art Tucker; 2.65% Nicotiana forgetiana (flower), JEOR 7:265(1995); 2.00% Rhus coriaria; 0.83% Sideritis amasiaca 81



100



O



E



80



E



H



60 40 41 67



55



20 40



95



60



80



152 100



120



140



160



RT: 20.88 AI: 1315 KI: 1317 Hexenyl tiglate CAS#: 120603-00-1 MF: C11 H18 O2 FW: 182 MSD LIB#: 1937 CN: 2-butenoic acid, 2-methyl-, (3E)-3-hexenyl ester, (2E)Synonyms: hexenyl tiglate Source: Bedoukian Res. ex JJ Brophy 100



67



55



80



82



E



O



60 40 20



41 40



101 60



80



100



120



140



160



180



200



E



Appendix III: Mass Spectra



349



RT: 20.90 AI: 1316 KI: 1317 Terpinyl acetate CAS#: 93836-50-1 MF: C12 H20 O2 FW: 196 MSD LIB#: 1562 CN: cyclohexanemethanol, α,α-dimethyl-4-methylene-, acetate Synonyms: none Source: Dragoco ex Norbert Braum 100



43 93



80 60



136



40



59



20



53 40



79



67



60



O-Ac



80



101 107



121



100



120



181 140



160



180



200



RT: 20.91 AI: 1316 KI: 1317 Terpinyl acetate CAS#: 20777-40-6 MF: C12 H22 O2 FW: 198 MSD LIB#: 1467 CN: cyclohexanemethanol, α,α,4-trimethyl-, acetate, cisSynonyms: p-menthan-8-ol acetate, cisSource: Dragoco ex Norbert Braum 100



43



80 60 40



O-Ac



55



81



67



20 40



60



95101



80



123 138 131



100



120



140



160



180



200



220



240



RT: 20.93 AI: 1316 KI: 1318 Citral CAS#: 75128-97-1 MF: C12 H22 O2 FW: 198 MSD LIB#: 451 CN: 2,6-octadiene, 1,1-dimethoxy-3,7-dimethyl-, (Z)Synonyms: dimethoxy nerol Source: Aldrich Chem. ex H. Hills 100



41



80 69



60 40



83



55



20 40



123 98



60



80



100



107



134141 151 120



140



166 160



183 180



198 200



Adams: Essential Oil Components by GC/MS



350



RT: 20.94 AI: 1316 KI: 1318 Patchenol CAS#: 58437-72-2 MF: C11 H18 O FW: 166 MSD LIB#: 1237 CN: ethanol, 2-(3,3-dimethylbicyclo(2.2.1)hept-2-yildene)-, (2Z)Synonyms: camphene methanol, 8Source: ref. cpd. ex P. Weyerstahl 100



41



Z



OH



107



80



79



67



60



91



55



40



123



20 40



60



80



100



120



135



166



148 140



160



180



RT: 20.96 AI: 1317 KI: 1319 Cycloisolongifolene CAS#: 74842-33-4 MF: C15 H22 FW: 202 MSD LIB#: 536 CN: 2,3b-methano-3bH-cyclopenta(1,3)cyclopropa(1,2)benzene, 1,2,3,3a,4,5-hexahydro1,1,4,4-tetramethylSynonyms: none Source: ref. cpd. ex P. Weyerstahl 131



100



117



80 41



91



105



202



60



145



69 77



40



H



159



H



53



20



187 173



40



60



80



100



120



140



160



180



200



RT: 21.00 AI: 1318 KI: 1319 Cinnamaldehyde CAS#: 101-39-3 MF: C10 H10 O FW: 146 MSD LIB#: 1686 CN: 2-propenal, 2-methyl-3-phenylSynonyms: α-methyl cinnimal, 2-methyl-3-phenylacrolein Source: Aldrich Chem. 117



100



O



145



80 91



60 40



51



63



78 103



20 40



60



80



100



131 120



140



Appendix III: Mass Spectra



351



RT: 21.01 AI: 1318 KI: 1320 Pinanediol CAS#: 18680-27-8 MF: C10 H18 O2 FW: 170 MSD LIB#: 1299 CN: bicyclo(3.1.1)heptane-2,3-diol, 2,6,6-trimethyl-, (1R-(1α,2α,3α,5α))Synonyms: pinene glycol, cis-αSource: Aldrich Chem. 100



43



OH



80 60 40



99



71



55



81



20 40



60



OH



111



93



80



100



126



137



120



140



160



180



RT: 21.02 AI: 1318 KI: 1320 Methyl thujate CAS#: 54598-10-6 MF: C11 H14 O2 FW: 178 MSD LIB#: 1864 CN: 1,3,6-cycloheptatriene-1-carboxylic acid, 5,5-dimethyl-,methyl ester Synonyms: thujic acid, methyl ester; Source: Quest Intl. ex Robin Clery 163



100



O-Me



80



91 119



60 40 20



77 41



51



105 131



59



40



O



60



80



100



120



147



140



178 160



180



RT: 21.04 AI: 1319 KI: 1320 Dihydro citronellol acetate CAS#: 20780-49-8 MF: C12 H24 O2 FW: 200 MSD LIB#: 592 CN: 1-octanol, 3,7-dimethyl-, acetate Synonyms: dihydro citronellyl acetate; tetrahydro geranyl acetate Source: ref. cpd. ex E. von Rudloff 100



43



80 60 55



40 20



70 83



40



60



80



97 100



111



140 120



140



160



180



200



Adams: Essential Oil Components by GC/MS



352



RT: 21.04 AI: 1319 KI: 1320 Dimethyl phenethyl acetate CAS#: 151-05-3 MF: C12 H16 O2 FW: 192 MSD LIB#: 611 CN: benzene ethanol, α,α, dimethyl-, acetate Synonyms: dimethylbenzylcarbinol acetate Source: Aldrich Chem. 100



O



43



80



O



60 40 59



20



51 40



91



117



65



60



132



101 80



100



120



140



160



180



200



RT: 21.05 AI: 1319 KI: 1321 Verbanol acetate CAS#: 73366-10-6 MF: C12 H20 O2 FW: 196 MSD LIB#: 1542 CN: bicyclo(3.1.1)heptan-2-ol, 4,6,6-trimethyl-, acetate,(1α,2β,4α,5α)Synonyms: none Source: acetylation of verbanols(6314) 100



43



O-Ac



80 60



93



40



121



85



55



107



67



20 40



60



80



100



136 120



154



140



160



180



200



RT: 21.07 AI: 1319 KI: 1321 Decadienol CAS#: 18409-21-7 MF: C10 H18 O FW: 154 MSD LIB#: 2106 CN: 2,4-decadien-1-ol, (2E,4E)Synonyms: none Source: Bedoukian Res. 100



41



E



55



80



83



60



E



HO



67



40 97



20 40



60



80



100



154 110



136 120



140



160



Appendix III: Mass Spectra



353



RT: 21.07 AI: 1319 KI: 1321 Hexenyl tiglate CAS#: 67883-79-8 MF: C11 H18 O2 FW: 182 MSD LIB#: 1936 CN: hexenyl tiglate Synonyms: hexenyl tiglate Source: Bedoukian Res. ex JJ Brophy; 20.30% Gardenia jasminoides, p.90, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 3.70% Lonicera japonica; 0.40% Hyacinthus orientalis 100



67



55



80



82



O



O



Z



E



60 40 20



41



101



40



60



80



100



120



140



160



180



200



RT: 21.11 AI: 1320 KI: 1322 Hexyl 2-methyl-3-pentenoate CAS#: 58625-94-8 MF: C12 H22 O2 FW: 198 MSD LIB#: 2196 CN: 3-pentenoic acid, 2-methyl-, hexyl ester, (Z)Synonyms: none Source: Bedoukian Res. 100



O



43 H3C(H2C)5



80



O



69



60



Z



40 20



57 40



85



60



99



80



100



114 183



129 120



140



160



180



198 200



RT: 21.16 AI: 1321 KI: 1323 Nonyne CAS#: 13257-44-8 MF: C11 H20 O2 FW: 184 MSD LIB#: 2115 CN: 2-nonyne, 1,1-dimethoxySynonyms: none Source: Bedoukian Res. 153



100



O-Me H3C-(H2C)5 O-Me



80 60 40 41 55



20



69



79



93 127



40



60



80



100



120



169



139 140



160



183 180



200



Adams: Essential Oil Components by GC/MS



354



RT: 21.17 AI: 1322 KI: 1324 Undec-(9Z)-en-1-al CAS#: 390745-03-6 MF: C11 H20 O FW: 168 CN: 9-undecenal, (9Z)Synonyms: none Source: Givaudan ex Jian-Qin Cu, Kunming 100



41



MSD LIB#: 1521



O



Z



55



(CH2)7



80 60 67



40



82



20 40



60



95



80



111



100



121



150



135



120



140



160



180



RT: 21.18 AI: 1322 KI: 1324 Jasmonol CAS#: 156316-87-9 MF: C11 H20 O FW: 168 MSD LIB#: 2026 CN: cyclopentanol, 2-(1E)-1-hexenyl-, (1R,2S)Synonyms: none Source: Bedoukian Res. ex JJ Brophy E



84



100 80 60 41



67



55



OH



97



40



121



20



107 40



60



80



100



139 120



150



140



168 160



180



RT: 21.19 AI: 1322 KI: 1324 Methyl geranate CAS#: 2349-14-6 MF: C11 H18 O2 FW: 182 MSD LIB#: 1133 CN: 2,6-octadienoic acid, 3,7-dimethyl-, methyl ester Synonyms: methyl geraniate Source: Neocallotropis pancheri oil ex P. Raharivelomanana; 0.80% Laurus nobilis, Acta Bot. Sinica 32:878(1990); 0.70% Aloysia triphylla; 0.66% Rosa damascena 100



69 O



41



80 O-Me



60 40 20 40



114



83



53



123 60



80



100



120



139 140



151



182 160



180



200



Appendix III: Mass Spectra



355



RT: 21.23 AI: 1323 KI: 1325 Methyl decanoate CAS#: 110-42-9 MF: C11 H22 O2 FW: 186 MSD LIB#: 1091 CN: decanoic acid, methyl ester Synonyms: methyl caprate; capric acid, methyl ester Source: ref. cpd. ex E. von Rudloff; 4.10% Amomum ptycholimatum, p. 333, in: Flav. & Frag.: A World Persp., Lawrence, etal. (eds.), Proc. 10th Int. Cong. Ess. Oils, Elsevier, Amsterdam(1988); 3.49% Magnolia grandiflora; 2.51% Humulus lupulus 74



100 80 60 40



87



43 55



20



101 40



60



80



143



129



100



120



155



140



160



186 180



200



RT: 21.28 AI: 1324 KI: 1326 Phenyl ethyl oxyacetaldehyde CAS#: 41847-88-5 MF: C10 H12 O2 FW: 164 MSD LIB#: 1289 CN: acetaldehyde, (2-phenylethoxy)Synonyms: none Source: Aldrich Chem. ex Art Tucker 105



100



O O



80



H



60 91



40



45



20



79



51



65 135



40



60



80



100



120



140



160



180



RT: 21.29 AI: 1324 KI: 1326 Myrtenyl acetate CAS#: 1079-01-2 MF: C12 H18 O2 FW: 194 MSD LIB#: 1121 CN: bicyclo(3.1.1)hept-2-ene-2-methanol, 6,6-dimethyl-, acetate,(1S) Synonyms: 2-pinen-10-ol, acetate Source: acetylation of myrtenol (6115); 35.90% Myrtus communis (leaf), JEOR 3:173(1991); 33.00% Myrtus communis (unripe fruit); 6.50% Egletes viscosa 91



100 80



43



60 40



119



20



53 40



65 60



79 80



108 100



134 120



140



152 160



180



200



Adams: Essential Oil Components by GC/MS



356



RT: 21.30 AI: 1325 KI: 1327 Mentha-1,4-dien-7-ol CAS#: 22539-72-6 MF: C10 H16 O FW: 152 MSD LIB#: 2180 CN: 1,4-cyclohexadiene-1-methanol, 4-(1-methylethyl)Synonyms: none Source: Rhodiola rosa roots ex. Jan Karlsen, Norway; 0.70% Hedyotis diffusa, JEOR 7:537(1995); 0.38% Citrus sinensis; 0.19% Daucus corota 79



100 80



OH



43 91



60 40 20



51



105



65



40



60



80



134



121



100



152



120



140



160



RT: 21.36 AI: 1326 KI: 1329 Dihydro carveol acetate CAS#: 160868-58-6 MF: C12 H20 O2 FW: 196 MSD LIB#: 598 CN: cychexanol, 2-methyl-5-(1-methylethenyl)-, acetate, (1α,2β,5β)Synonyms: none Source: ref. cpd. ex E. von Rudloff 100



43



80



O-Ac



60 93



40 67



55



20



107



79



121



136 154



40



60



80



100



120



140



RT: 21.37 AI: 1326 KI: 1328 Limonene aldehyde CAS#: 6784-13-0 MF: C11 H18 O FW: 166 CN: 3-cyclohexene-1-propanal, β,4-dimethylSynonyms: p-menth-1-ene-9-carboxaldehyde Source: Takita Chem. ex Art Tucker



196



160



180



200



MSD LIB#: 1006



93



100



67



80 41 60



79



55



40



106 121



20



148



133



166 40



60



80



100



120



140



160



180



Appendix III: Mass Spectra



357



RT: 21.37 AI: 1326 KI: 1328 Silphiperfol-5-ene CAS#: 138752-24-6 MF: C15 H24 FW: 204 MSD LIB#: 635 CN: cyclopenta(c)pentalene, 1,3a,4,5,5a,6,7,8-octahydro-1,2,3a,6-tetramethyl-,(1S,3aS,5aS,6R,8aR)Synonyms: silphiperfol-5-ene B Source: Echinopos giganteus oil ex P. Weyerstahl 175



100 80 60 40 41 55



20 40



67



91



77



60



80



121 133



105



147



100



120



140



RT: 21.39 AI: 1327 KI: 1329 Hasmigone CAS#: 000-00-0 MF: C11 H18 O FW: 166 CN: cyclopentanone, 2-(2-hexenyl)-, (2Z)Synonyms: none Source: Bedoukian Chem. ex Art Tucker



H



160



180



200



MSD LIB#: 765



Z



84



100 80



204



189



161



41



60



O



55



67



40



95



20



123 137



40



60



80



100



120



140



148



166 160



180



RT: 21.39 AI: 1327 KI: 1329 Isobutyl benzoate CAS#: 120-50-3 MF: C11 H14 O2 FW: 178 MSD LIB#: 858 CN: benzoic acid, 2-methylpropyl ester Synonyms: none Source: Aldrich Chem.; 1.15% Chenopodium ambrosioides, JEOR 7:221(1995); 0.30% Empleurum fragrans; 0.01% Spartium junceum (absolute) O



105



100



O



80 60



77



40



123



56



20 41 135 40



60



80



100



120



140



160



180



Adams: Essential Oil Components by GC/MS



358



RT: 21.43 AI: 1328 KI: 1330 Jasmonol CAS#: 156316-90-4 MF: C11 H20 O FW: 168 MSD LIB#: 2027 CN: cyclopentanol, 2-(1E)-hexenyl-, (1R,2R)Synonyms: none Source: Bedoukian Res. ex JJ Brophy 84



100 80 60



41



E



67



97



55



OH



121



40 20



107 40



60



80



100



139 120



150



140



168 160



180



RT: 21.44 AI: 1328 KI: 1330 Menthol CAS#: 3564-95-2 MF: C10 H20 O2 FW: 172 MSD LIB#: 2015 CN: cyclohexanemethanol, 2-hydroxy-α,α,4-trimethyl-,(1R,2S,4R)Synonyms: neomenthoglycol; PMD 38; Source: ref. cpd. ex JJ Brophy 100



81



59



OH HO



80 60



43



96



40 67



20 40



60



80



111 121



139



120



140



100



154 160



180



RT: 21.45 AI: 1328 KI: 1330 Patchenol CAS#: 58437-71-1 MF: C11 H18 O FW: 166 MSD LIB#: 1238 CN: ethanol, 2-(3,3-dimethylbicyclo(2.2.1)hept-2-yidiene)-, (2E)Synonyms: none Source: ref. cpd. ex P. Weyerstahl 100



OH



41



80



67



60



79



107



E



91



55



40



123



133



20



148 40



60



80



100



120



140



166 160



180



Appendix III: Mass Spectra



359



RT: 21.45 AI: 1328 KI: 1330 Verbanol acetate CAS#: 73366-12-8 MF: C12 H20 O2 FW: 196 MSD LIB#: 1543 CN: bicyclo(3.1.1)heptan-2-ol, 4,6,6-trimethyl-, acetate,(1α,2β,4β,5α)Synonyms: none Source: acetylation of verbanols(6314) 100



43 O-Ac



80 60 40



85 93



55



20



121 107



67 40



60



80



100



136 120



154



140



160



180



200



RT: 21.51 AI: 1329 KI: 1332 Piperonal CAS#: 120-57-0 MF: C8 H6 O3 FW: 150 MSD LIB#: 1331 CN: 1,3-benzodioxole-5-carboxaldehyde Synonyms: heliotropin; geliotropin Source: Aldrich Chem. ex H. Hills; 1.40% Eucalyptus lehmanni, FFJ 5:91(1990); 0.24% Cinnamomum micranthum; 0.10% Piper nigrum 149



100 80



O



O



O



60 40 20



91



53 40



H



121



63



60



80



100



120



RT: 21.52 AI: 1330 KI: 1332 Anisyl formate CAS#: 122-91-8 MF: C9 H10 O3 FW: 166 CN: benzenemethanol, 4-methoxy-, formate Synonyms: none Source: Aldrich Chem.



140



160



MSD LIB#: 176



121



100



O



80 60



Me-O



40



77



20



51 40



63 60



166



91 135



80



100



120



140



160



180



O



Adams: Essential Oil Components by GC/MS



360



RT: 21.54 AI: 1330 KI: 1332 Hexyl tiglate CAS#: 16930-96-4 MF: C11 H20 O2 FW: 184 MSD LIB#: 45 CN: 2-butenoic acid, 2-methyl-, hexyl ester, (E)Synonyms: crotonic acid, 2-methyl-, hexyl ester (E)Source: Aldrich Chem.; 0.46% Lavandula angustifolia, Perf. & Flav. 9:49(1984); 0.38% Lavandula x hybrida; 0.20% Chamomilla recutita 101



100 80



83



60 40



E



O



55



O



43



20



69 40



60



169



127 80



100



120



140



160



184 180



200



RT: 21.56 AI: 1330 KI: 1333 Menth-1-en-7-al CAS#: 160152-34-1 MF: C10 H14 O2 FW: 166 MSD LIB#: 1422 CN: 1-cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)-3-oxoSynonyms: none Source: Solidago graminifolia oil ex P. Weyerstahl 124



100 80 41



95



68



60 55



40



77



20 40



60



80



100



151



138



105 120



140



166 160



180



RT: 21.63 AI: 1332 KI: 1334 Piperitol acetate CAS#: 112028-22-5 MF: C12 H20 O2 FW: 196 MSD LIB#: 1325 CN: 2-cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, acetate, cisSynonyms: none Source: acetylation of cis-piperitol(6433) 100



43 93



80



121 84



60



O-Ac



40 69



55



20 40



136



60



154



111 80



100



120



140



160



196 180



200



Appendix III: Mass Spectra



361



RT: 21.68 AI: 1333 KI: 1336 Hasmigone CAS#: 868693-38-3 MF: C11 H18 O FW: 166 CN: cyclopentanone, 2-(2-hexenyl)-, (E)Synonyms: none Source: Bedoukian Res. ex Art Tucker



MSD LIB#: 766



84



100 80 60



41 55



67



40



95



20 40



60



80



123



100



137



120



166



148



140



160



180



RT: 21.70 AI: 1334 KI: 1336 Presilphiperfol-7-ene CAS#: 80931-09-5 MF: C15 H24 FW: 204 MSD LIB#: 636 CN: 1H-cyclopent(cd)indene, 2,2a,3,4,4a,5,6,7-octahydro-1,1,2a,5-tetramethyl-, (2aS,4aS,5R)Synonyms: none Source: Echinopos giganteus oil ex P. Weyerstahl 119



100 80 60 41



91



147



105



189



161



204



133



40



77



55



175



65



20 40



60



80



H



100



120



140



160



180



200



RT: 21.72 AI: 1334 KI: 1337 Anthranilate CAS#: 134-20-3 MF: C8 H9 N O2 FW: 151 MSD LIB#: 179 CN: benzoic acid, 2-amino-, methyl ester Synonyms: 2-carbomethoxyaniline; methyl 2-aminobenzoate Source: Neroil oil ex Alan F. Thomas 119



100 80



151



92



60 40



65



20



52 40



60



80



100



120



140



160



Adams: Essential Oil Components by GC/MS



362



RT: 21.72 AI: 1334 KI: 1337 Methyl ο-anisate CAS#: 606-45-1 MF: C9 H10 O3 FW: 166 CN: benzoic acid, 2-methoxy-, methyl ester Synonyms: dimethyl salicylate Source: Aldrich Chem.



MSD LIB#: 1692



135



100



O



80



O-Me



Me-O



77



60 40



92



63



166



105



51



20



120



40



60



80



100



151



120



140



160



180



RT: 21.73 AI: 1334 KI: 1337 Linalool propanoate CAS#: 144-39-8 MF: C13 H22 O2 FW: 210 MSD LIB#: 1634 CN: 1,6-octadien-3-ol, 3,7-dimethyl-, propanoate Synonyms: 1,6-octadien-3-ol Source: Aldrich Chem.; 4.96% Artemisia afra, Pharmazie 49:935(1994); 0.36% Citrus limon; 0.12% Lavandula angustifolia 93



100



O



80 O



60



41



57 69



40



121



80



20



107 40



60



80



100



136 120



154



140



160



180



200



220



RT: 21.76 AI: 1335 KI: 1337 Benzenemethanol CAS#: 623-05-2 MF: C7 H8 O2 FW: 124 MSD LIB#: 1998 CN: benzenemethanol, 4-hydroxySynonyms: gastrodigenin; p-methylolphenol; α-hydroxy-p-cresol Source: Aldrich Chem. ex JJ Brophy 124



100



OH



95



80



77



60



107



40 20 41 40



65



51



OH



60



80



100



120



140



Appendix III: Mass Spectra



363



RT: 21.77 AI: 1335 KI: 1338 Elemene CAS#: 20307-84-0 MF: C15 H24 FW: 204 MSD LIB#: 308 CN: cyclohexene, 4-ethenyl-4-methyl-3-(1-methylethenyl)-1-(1-methylethyl)-, 3R-trans-) Synonyms: p-menth-3-ene, 2-isopropenyl-1-vinyl, transSource: Black pepper distillation; 28.79% Commiphora myrrha, 9th Int. Cong. of Ess. Oils, Paper #400, Singapore (1983); 6.40% Baccharis dracunculifolia; 5.27% Myrica cerifera (leaf) 121



100 93



80



136



60 40 41 20



161



77 53



40



105



67 60



148 80



100



120



140



189



175 160



180



204 200



RT: 21.80 AI: 1336 KI: 1338 Phenyl pentan-3-one CAS#: 20795-51-1 MF: C11 H14 O FW: 162 MSD LIB#: 119 CN: 3-pentanone, 1-phenylSynonyms: ethyl phenethyl ketone Source: Amomyrtus meli oil ex P. Weyerstahl 91



100 80



105



O



57



60 40



51



20 40



65 60



162



133



77



80



100



120



RT: 21.82 AI: 1336 KI: 1339 Isosafrole CAS#: 17627-76-8 MF: C10 H10 O2 FW: 162 CN: benzodioxole Synonyms: none Source: Aldrich Chem.



140



160



180



MSD LIB#: 886



162



100 80 60 131



104



40 51



20 40



77 63 60



91 80



147 100



120



140



160



180



Adams: Essential Oil Components by GC/MS



364



RT: 21.85 AI: 1337 KI: 1340 Evodone CAS#: 30557-66-5 MF: C10 H12 O2 FW: 164 MSD LIB#: 702 CN: 4(5H)-benzofuranone, 6,7-dihydro-3,6-dimethylSynonyms: p-mentha-4,8-dien-3-one, 5,9-epoxySource: Euodia hortensis oil ex JJ Brophy; 44.00% Euodia hortensis (flower), FFJ 1:17(1985); 25.00% Euodia hortensis (leaf); 0.80% Dracocephalum kotschyi 122



100



O



80 60



164



94



O



40 20



66 41



51



77



40



60



149



135



80



100



120



140



160



180



RT: 21.90 AI: 1338 KI: 1341 Citral CAS#: 75128-98-2 MF: C12 H22 O2 FW: 198 MSD LIB#: 452 CN: 2,6-octadiene, 1,1-dimethyoxy-3,7-dimethyl-, (E)Synonyms: dimethoxy geraniol Source: Aldrich Chem. ex Art Tucker 100



41 69



80 60 40



83



55



20



98



123



91 40



60



80



129135 141 151



107 100



120



140



RT: 21.90 AI: 1338 KI: 1341 Indanol CAS#: 1470-94-6 MF: C9 H10 O FW: 134 CN: 1H-inden-5-ol, 2,3-dihydroSynonyms: 5-hydroxyindane Source: Aldrich Chem.



167 160



180



200



MSD LIB#: 838



133



100 80 60 40



105



77



51



20



66 40



60



115



91 80



100



120



140



Appendix III: Mass Spectra



365



RT: 21.92 AI: 1339 KI: 1341 Benzenemethanol CAS#: 620-24-6 MF: C7 H8 O2 FW: 124 MSD LIB#: 2001 CN: benzenemethanol, 3-hydroxySynonyms: hydroxybenzyl alcohol, 3Source: Aldrich Chem. ex JJ Brophy



80



95



77



60 40



HO



20 41



105



65



51



40



60



80



100



RT: 21.92 AI: 1339 KI: 1341 Octanediol CAS#: 629-41-4 MF: C8 H18 O2 FW: 146 CN: 1,8-octanediol Synonyms: none Source: Pfaltz & Bauer ex JJ Brophy 100 80



OH



124



100



120



MSD LIB#: 2008



67



55



140



HO OH



41



82



60 40 20



95 40



60



80



100



120



140



RT: 21.95 AI: 1339 KI: 1342 Butanone CAS#: 5355-63-5 MF: C10 H12 O2 FW: 164 MSD LIB#: 1112 CN: 2-butanone, 3-hydroxy-4-phenylSynonyms: none Source: Mimusops elengi ex KC Wong, Malaysia O



91



100



103



80 60



121



OH



43



40



65



20



146



77



51 40



131 60



80



100



120



140



160



180



Adams: Essential Oil Components by GC/MS



366



RT: 21.95 AI: 1339 KI: 1342 Carvyl acetate CAS#: 1134-95-8 MF: C12 H18 O2 FW: 194 MSD LIB#: 368 CN: 2-cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, acetate, transSynonyms: p-mentha-6,8-dien-2-ol, acetate, transSource: SCM Chems. ex H. Hills; 5.90% Mentha spicata, FFJ 1:105(1986); 0.99% Mentha aquatica x viridis; 0.84% Hyptis mutabilis 100



43



80



109 119



84



O-Ac



152



91



60 40



77



55



20 40



134



67



194



60



80



100



120



140



160



180



200



RT: 21.96 AI: 1340 KI: 1342 Mentho thiophene CAS#: 103275-89-4 MF: C10 H14 S FW: 166 MSD LIB#: 2193 CN: benzo(b)thiophene, 4,5,6,7-tetrahydro-3,6-dimethylSynonyms: none Source: ref. cpd. ex P. Weyerstahl 124



100



S



80 60 40



166



20



45 51 40



91



77 60



80



111 100



134 120



RT: 21.97 AI: 1340 KI: 1342 Jasmatone CAS#: 13074-65-2 MF: C11 H20 O FW: 168 CN: cyclopentanone, 2-hexylSynonyms: dihydroisojasmone Source: Bedoukian Res.



140



151 160



180



MSD LIB#: 2138



84



100 80



O



60 40 41 20



55



97



69 40



60



126 80



100



120



168



139 140



160



180



Appendix III: Mass Spectra



367



RT: 21.98 AI: 1340 KI: 1343 Piperitenone CAS#: 491-09-8 MF: C10 H14 O FW: 150 MSD LIB#: 1064 CN: 2-cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)Synonyms: pulespenone; 3-terpinolenone Source: Mentha verticillata oil ex M. Maffei, Italy; 40.40% Calamintha nepeta, JEOR 3:7(1991); 34.00% Mentha cervina; 14.70% Ziziphora hispanica 107



100



150



80 60 41



91 79



53



40



121



65



20 40



O



135 115



60



80



100



120



140



160



RT: 22.00 AI: 1340 KI: 1343 Verbanol acetate CAS#: 73366-09-3 MF: C12 H20 O2 FW: 196 MSD LIB#: 1540 CN: bicyclo(3.1.1)heptan-2-ol, 4,6,6-trimethyl-, acetate,(1α,2α,4α,5α)Synonyms: none Source: acetylation of verbanols(6314) 100



43



O-Ac



80 60 40



93



85



55



121 107



67



20 40



60



127 80



100



136



120



140



160



180



200



RT: 22.09 AI: 1342 KI: 1345 Nicotine CAS#: 54-11-5 MF: C10 H14 N2 FW: 162 MSD LIB#: 1150 CN: pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)Synonyms: none Source: Aldrich Chem.; 25.92% Nicotiana rustica (flower), JEOR 7:265(1995) 84



100



N



80 60 40 42 20



133 51



40



65 60



161



119



92 80



N



100



120



140



160



180



Adams: Essential Oil Components by GC/MS



368



RT: 22.10 AI: 1343 KI: 1346 Piperitol acetate CAS#: 91159-15-8 MF: C12 H20 O2 FW: 196 MSD LIB#: 1326 CN: 2-cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, acetate, transSynonyms: none Source: acetylation of trans-piperitol(6433) 100



43



80



84



60 40



77



55



20 40



121



93



136



69



154



105111



60



80



100



120



140



RT: 22.13 AI: 1343 KI: 1346 Benzyl butanoate CAS#: 103-37-7 MF: C11 H14 O2 FW: 178 CN: butanoic acid, phenylmethyl ester Synonyms: benzyl butyrate Source: Aldrich Chem.



196



160



180



200



MSD LIB#: 74



91



100



O



108



80



O



60 40



43



20



65



51



71



178 79 160



40



60



80



100



120



140



160



180



RT: 22.18 AI: 1345 KI: 1347 Silphinene CAS#: 74284-57-4 MF: C15 H24 FW: 204 MSD LIB#: 2167 CN: cyclopenta(c)pentalene,1,2,3,3a,4,5,5a,6-octahydro-1,4,4,5a-tetramethyl-, [1R-(1α,3aα,5aβ,8aR*)]Synonyms: none Source: Artemisia anna roots, Vietnam ex HJ Woerdenbag 91



100



105



80 60 40



41



147



189



119



77



55



133



161



67



20



204 175



40



60



80



100



120



140



160



180



200



Appendix III: Mass Spectra



369



RT: 22.20 AI: 1345 KI: 1348 Silphiperfol-5-ene CAS#: 138752-23-5 MF: C15 H24 FW: 204 MSD LIB#: 637 CN: cyclopenta(c)pentalene, 1,3a,4,5,5a,6,7,8-octahydro-1,2,3a,6-tetramethyl-,(1R,3aS,5aS,6R,8aR)Synonyms: none Source: Echinopos giganteus oil ex P. Weyerstahl 100



41



91 105



80 60



119



133



147



175



189



204



77



55



40



161



67



20



H



40



60



80



100



120



140



160



180



200



RT: 22.24 AI: 1346 KI: 1349 Phenol CAS#: 91-10-1 MF: C8 H10 O3 FW: 154 MSD LIB#: 1269 CN: phenol, 2,6-dimethoxySynonyms: syringol Source: ref. cpd. ex E. von Rudloff 154



100 80



139



60 40



93



65



51



111



79



20 40



60



80



100



120



140



160



RT: 22.26 AI: 1346 KI: 1349 Terpinyl acetate CAS#: 80-26-2 MF: C12 H20 O2 FW: 196 MSD LIB#: 948 CN: 3-cyclohexene-1-methanol, α,α,4-trimethyl-, acetate Synonyms: p-menth-1-en-8-ol, acetate Source: Juniperus squamata, India, oil ex P. Weyerstahl; 43.00% Elettaria cardamomum, Phytochem. 10:177(1971); 30.50% Eucalyptus diversicolor; 26.90% Lavendula x hybrida 100



43 121



80



93



60



136



40 20



53 40



59 67



79



60



80



107 100



120



140



160



180



200



Adams: Essential Oil Components by GC/MS



370



RT: 22.30 AI: 1347 KI: 1350 Acetophenone Source: Bedoukian Res. 135



100 80



E



107



60 43 40



O



150



91



20 40



55 65



79



60



80



123 163 173 100



120



140



160



180



191



206 200



Adams: Essential Oil Components by GC/MS



474



RT: 27.94 AI: 1479 KI: 1480 Cabreuva oxide D CAS#: 107602-52-8 MF: C15 H24 O FW: 220 MSD LIB#: 341 CN: 1H-2-benzopyran, 3-ethenyl-3,4,4a,7,8,8a-hexahydro-1,1,3,6-tetramethyl-, (3S-(3α,4aβ,8aβ))Synonyms: none Source: ref. cpd. ex P. Weyerstahl; 0.40% Baccharis dracunculifolia, FFJ 11:15(1996) 94



100



H



80 60



O



40 43 20



79 55



40



H



69



60



135



107 80



100



120



147



140



162



205



187



160



180



200



220 220



RT: 27.96 AI: 1479 KI: 1480 Curcumene CAS#: 644-30-4 MF: C15 H22 FW: 202 MSD LIB#: 1379 CN: benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methylSynonyms: α-curcumene Source: Sandalwood oil ex Brian Lawrence; 41.40% Curcuma xanthorrhiza, FFJ 7:19(1992); 27.84% Curcuma angustifolia; 27.10% Zingiber officinale 119



100



132



80 60 41 40



105 55



20 40



91 69 77 83



60



80



202



145 159 100



120



140



160



187 180



200



RT: 27.96 AI: 1479 KI: 1480 Ionol CAS#: 436099-48-8 MF: C14 H24 O FW: 208 MSD LIB#: 2123 CN: 1-penten-3-ol, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (1E)Synonyms: none Source: Bedoukian Res. 57



100



OH



80



E



60



95



40 20



123



41 67 40



60



81 80



105 100



152 137



120



140



161 160



175 180



208



190 200



Appendix III: Mass Spectra



475



RT: 27.97 AI: 1479 KI: 1481 Amorpha-4,7(11)-diene CAS#: 486998-53-2 MF: C15 H24 FW: 204 MSD LIB#: 1899 CN: naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethylidene)-, (4S,4aR,8aS)Synonyms: none Source: Maque oil ex Winfried Koenig 161



100 80 60 41 40



91 55



20 40



105 119 133



67



60



H



204



81



80



100



120



189 147



140



H



175 160



180



200



RT: 27.99 AI: 1480 KI: 1481 Germacrene D CAS#: 23986-74-5 MF: C15 H24 FW: 204 MSD LIB#: 500 CN: 1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, (S-(E,E)-)Synonyms: germacra-1(10),4(15),5-triene Source: Cubeb oil ex E. von Rudloff; 81.00% Carum carvi (herb), FFJ 2:83(1987); 55.90% Cinopodium vulgare; 48.39% Salvia sclarea 100 41



91



161



105



80 79



60 55



40



119



E E



67



133



20



204



147 40



60



80



100



120



140



160



180



200



RT: 28.00 AI: 1480 KI: 1481 Ionone CAS#: 101325-32-0 MF: C14 H22 O FW: 206 MSD LIB#: 845 CN: 3-buten-2-one, 4-(2,2-dimethyl-6-methylenecyclohexyl)-, nonomethyl deriv. Synonyms: cis-γ-irone, 10-methyl-β-ionol Source: K & K Chem. ex H. Hills 135



100



O



E



80 107



60 43 40 20 40



91 55 65



79



60



80



150



123 163 173 100



120



140



160



180



191



206 200



Adams: Essential Oil Components by GC/MS



476



RT: 28.02 AI: 1480 KI: 1482 Cyclogeranyl acetate CAS#: 69842-11-1 MF: C12 H20 O2 FW: 196 MSD LIB#: 531 CN: 2-cyclohexene-1-methanol, 2,6,6-trimethyl-, acetate Synonyms: cyclogeraniol acetate Source: acetylation of α-cyclogeraniol(6110) 100



43



59



80 60



70



40



83



40



60



123



98



20 80



141



100



120



140



161



189



160



180



200



RT: 28.03 AI: 1481 KI: 1482 Widdra-2,4(14)-diene CAS#: 847374-87-2 MF: C15 H24 FW: 204 MSD LIB#: 1922 CN: 1H-benzocycloheptene, 2,3,4,4a,5,6,7,9a-octahydro-1,1,4a-trimethyl7-methylene-, (4aR,9aR)Synonyms: none Source: Cupressus macrocarpa oil ex Larry Cool 100



41



91



80 55



60



69



H



105



79



111 119



40



204



148



20 40



60



80



100



120



189



161



133



140



175 160



180



200



RT: 28.04 AI: 1481 KI: 1482 Curcumene CAS#: 28976-68-3 MF: C15 H24 FW: 204 MSD LIB#: 768 CN: 1,3-cyclohexadiene, 1-(1,5-dimethyl-4-hexenyl)-4-methylSynonyms: none Source: Helichrysum oil ex P. Weyerstahl; 10.40% Helichrysum italicum, p. 177, in: Progress in Essential Oil Research (Proc. Intern. Symp. on Ess. Oils), E.-J. Brunke Ed., Gruyter Publ., Berlin(1986); 6.40% Populus deltoides; 1.81% Santolina chamaecyparissus 119



100 80 60



93



41



40



55



20 40



204



105



60



69



77 134 80



100



120



147



140



161 160



189 180



200



Appendix III: Mass Spectra



477



RT: 28.05 AI: 1481 KI: 1482 Amorphane CAS#: 178737-43-4 MF: C15 H26 O FW: 222 MSD LIB#: 127 CN: 2,5-methano-2H-1-benzopyran, octahydro-2,8a-dimethyl-6-(1-methylethyl)-, (2R,4aS,5S,6S,8aR)Synonyms: 4,10-epoxy-muurolane Source: ref. cpd. ex P. Weyerstahl 100



43 H H



80



137



60 40 55



20



67



81



109



95



222 121



164



151 40



60



80



100



120



140



160



207



179 189 180



O



200



220



RT: 28.05 AI: 1481 KI: 1482 Himachalene CAS#: 53111-25-4 MF: C15 H24 FW: 204 MSD LIB#: 236 CN: 1H-benzocycloheptene,2,4a,5,6,7,9a-hexahydro-3,5,5,9-tetramethyl-, (4aS-cis)Synonyms: none Source: Artemisia vestita oil ex P. Weyerstahl; 10.50% Cedrus atlantica, JEOR 6:323(1994); 3.37% Pimpinella anisum; 2.82% Artemisia vestita 93



100



133



105



80 41



H



204



119



60



H



79 161



55



40



189



147



67



20



175 40



60



80



100



120



140



160



180



200



RT: 28.05 AI: 1481 KI: 1482 Menthyl lactate CAS#: 59259-38-0 MF: C13 H24 O3 FW: 228 MSD LIB#: 1083 CN: propanoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester,(1R-(1α,(R*),2β,5α))Synonyms: none Source: H & R Chem. ex Jian-Qin Cu, Kunming 83



100 80 60 40



55 41



69 95



20



123 40



60



80



100



120



139 140



160



180



200



220



240



Adams: Essential Oil Components by GC/MS



478



RT: 28.05 AI: 1481 KI: 1482 Vanillone, acetoCAS#: 498-02-2 MF: C9 H10 O3 FW: 166 CN: ethanone, 1-(4-hydroxy-3-methoxyphenyl)Synonyms: acetoguaiacone; apocynine Source: Aldrich Chem.



MSD LIB#: 1535



151



100



O



80 60 40



166 43



20



123 51



65



40



108



77



60



80



Me-O OH



136



100



120



140



160



180



RT: 28.07 AI: 1482 KI: 1483 Citronellol isobutanoate CAS#: 97-89-2 MF: C14 H26 O2 FW: 226 MSD LIB#: 456 CN: propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl ester Synonyms: citronellol isobutyrate Source: Pfaltz & Bauer ex Art Tucker 100



41



O



80 69



60



81



O



95



55



40



123 109



20 40



60



80



100



138 120



140



160



180



200



220



RT: 28.08 AI: 1482 KI: 1483 Decalactone CAS#: 7011-83-8 MF: C11 H20 O2 FW: 184 MSD LIB#: 1981 CN: 2(3H)-furanone, 5-hexyldihydro-5-methyl-, Synonyms: 4-methyldecanolid Source: Bedoukian Chem. ex JJ Brophy 99



100



O



O



80 60 40 20



43 55 40



71 60



129 80



100



120



169 140



160



180



200



Appendix III: Mass Spectra



479



RT: 28.09 AI: 1482 KI: 1483 Toluene CAS#: 14107-97-2 MF: C10 H14 O3 FW: 182 MSD LIB#: 1674 CN: benzene, 1,3,5-trimethoxy-2-methylSynonyms: none Source: Stockwellia sp. oil ex JJ Brophy 182



100



O-Me



80 60 40



69 77



53



20 40



60



139



120



140



109



91



80



121



100



151



167



Me-O



160



180



O-Me



200



RT: 28.12 AI: 1483 KI: 1484 Phenyl propyl butanoate CAS#: 80866-83-7 MF: C13 H18 O2 FW: 206 MSD LIB#: 1282 CN: butanoic acid, 2-phenylpropyl ester Synonyms: 2-phenylpropyl butyrate Source: Aldrich Chem. ex Art Tucker 118



100



O



80 60



71



43



O



40 20



77



51 40



91



60



80



105



100



120



140



160



180



200



RT: 28.12 AI: 1483 KI: 1484 Thujaplicin CAS#: 672-76-4 MF: C10 H12 O2 FW: 164 MSD LIB#: 1492 CN: 2,4,6-cycloheptatrien-1-one, 2-hydroxy-5-(1-methylethyl)Synonyms: 5-isopropyltropolone Source: ref. cpd. ex E. von Rudloff 121



100



149



80



164



60 40



77



20 41 40



65



51



91



103 135



60



80



100



120



140



160



180



Adams: Essential Oil Components by GC/MS



480



RT: 28.13 AI: 1483 KI: 1484 Amorphene CAS#: 20085-19-2 MF: C15 H24 FW: 204 MSD LIB#: 1316 CN: naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-(1R-(1α,4aβ,8aβ))Synonyms: cadina-4,9-diene, 1β,7βH-; zizanene Source: Pinus edulis resin ex Larry Cool; 16.50% Brachylaena hutchinsii, Dragoco Rept., 87-91(1973); 9.60% Alseuosmia macrophylla; 5.04% Eugenia banderensis leaf 105



100



H



80 60 41



94



40 53



20 40



80



100



120



H



204



133



65 60



161



119



77



148



140



175 160



189



180



200



RT: 28.14 AI: 1483 KI: 1484 Jasmone lactone CAS#: 14252-84-7 MF: C11 H18 O2 FW: 182 MSD LIB#: 2035 CN: 2(3H)-furanone, 5-(3-hexenyl)dihydro-5-methyl-, (3E)Synonyms: none Source: Bedoukian Res. 68



100



O



O



E



80 60 40



43



20



99 55



40



81 60



80



109



93



139 100



120



140



153



167



160



182 180



200



RT: 28.19 AI: 1485 KI: 1486 Prenyl benzoate CAS#: 5205-11-8 MF: C12 H14 O2 FW: 190 MSD LIB#: 2032 CN: 2-buten-1-ol, 3-methyl-, benzoate Synonyms: none Source: Bedoukian Res.; 1.94% Narcissus jonquilla, Shitsuryo Bunschi 3:202(1979); 0.82% Cananga odorata 105



100



O



80



O



68



60 40 41



77 51



20



85 40



60



80



131 100



120



190



145 140



160



180



200



Appendix III: Mass Spectra



481



RT: 28.20 AI: 1485 KI: 1486 Himachala-1,4-diene CAS#: 000-00-0 MF: C15 H24 FW: 204 MSD LIB#: 1863 CN: not assigned Synonyms: none Source: Juniperus chinensis wood oil ex Larry Cool 119



100 80 60



H



40 20



105 41



55



40



60



204



91



69 77



133



80



100



120



147



140



161



189



160



180



200



RT: 28.24 AI: 1486 KI: 1487 Benzyl acetylacetate CAS#: 5396-89-4 MF: C11 H12 O3 FW: 192 MSD LIB#: 285 CN: butanoic acid, 3-oxo-, phenylmethyl ester Synonyms: benzyl 3-oxobutanoate Source: Aldrich Chem.



60



O



91



100 80



O



O



107 43



40



58



65



51



20 40



79 164



60



80



100



120



140



192



160



180



200



RT: 28.25 AI: 1486 KI: 1487 Phenyl ethyl 2-methylbutanoate CAS#: 24817-51-4 MF: C13 H18 O2 FW: 206 MSD LIB#: 1285 CN: butanoic acid, 2-methyl-, 2-phenylethyl ester Synonyms: none Source: Aldrich Chem. ex Art Tucker



O



104



100



O



80 60 57



40 20 41 40



51



65 60



77 85 91 80



100



120



140



160



180



200



Adams: Essential Oil Components by GC/MS



482



RT: 28.28 AI: 1487 KI: 1488 Aristolochene CAS#: 26620-71-3 MF: C15 H24 FW: 204 MSD LIB#: 1882 CN: naphthalene, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethyl)-, (1R,7R,8aS)Synonyms: 4βH,5α-eremophila-9,11-diene Source: ref. cpd. ex Jan Demyttenaere 105



100



189



80 60 41 40



91 121



80



55



133



161



147



67



20



204



175 40



60



80



100



120



140



160



180



200



RT: 28.30 AI: 1487 KI: 1488 Ionone CAS#: 79-77-6 MF: C13 H20 O FW: 192 MSD LIB#: 843 CN: 3-buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)Synonyms: trans-β-ionone Source: Aldrich Chem.; 48.60% Lawsonia inermis (flower), JEOR 7:425(1995); 19.40% Osmanthus fragrans; 17.18% Cymbidium sinense 177



100 80 60 40



43



20



91



77 40



60



80



107 100



121



135



120



149 159



140



192



160



180



200



RT: 28.31 AI: 1487 KI: 1488 Jasmolactone CAS#: 1062323-04-9 MF: C10 H16 O2 FW: 168 MSD LIB#: 958 CN: 2H-pyran-2-one, tetrahydro-6-(3-pentenyl)-, (Z)Synonyms: none Source: Firmenich ex Jian-Qin Cu, Kunming 100 41



55



O



O



Z



80 68



60



81



40



108 93 99



20 40



60



80



100



150



132 120



140



168 160



180



Appendix III: Mass Spectra



483



RT: 28.34 AI: 1488 KI: 1489 Butylated hydroxy anisole CAS#: 25013-16-5 MF: C11 H16 O2 FW: 180 MSD LIB#: 332 CN: phenol, (1,1-dimetylethyl)-4-methoxySynonyms: antioxyne B; BHA; tert-butyl-4-methoxyphenol Source: Aldrich Chem.



OH



165



100



?



137



80 60



O-Me



180



40 20



41



53



65



40



60



77



91



80



107 115 124 100



150



120



140



160



180



200



RT: 28.35 AI: 1488 KI: 1489 Methyl biphenyl CAS#: 644-08-6 MF: C13 H12 FW: 168 MSD LIB#: 1653 CN: 1,1'-biphenyl, 4-methylSynonyms: biphenyl , p-phenyltoluene Source: Aldrich Chem. 168



100 80 60 40 20



63



51 40



89



74



60



80



152



115 100



128



120



139 140



160



180



RT: 28.36 AI: 1489 KI: 1489 Eudesma-6,11-diene CAS#: 194607-93-7 MF: C15 H24 FW: 204 MSD LIB#: 692 CN: naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-7-)1-methylethenyl)-. (1R,4aS,8aR)Synonyms: eudesmadiene Source: ref. cpd. ex P. Weyerstahl 108



100 41 80



91



55



60



79 119



40



67



20



H



133



147



161 175



40



60



80



100



120



140



160



180



189



204



200



Adams: Essential Oil Components by GC/MS



484



RT: 28.37 AI: 1489 KI: 1490 Selinene CAS#: 17066-67-0 MF: C15 H24 FW: 204 MSD LIB#: 420 CN: naphthalene, decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-, (4aR-(4aα,7α,8aβ))Synonyms: eudesma-4(14),11-diene; selina-4(14),11-diene; β-eudesmene Source: distillation of celery leaves, RP Adams #5942; 30.50% Apium graveolens, Pakistan J. Sci. Ind. Res. 19:243(1976); 17.39% Coleus aromaticus; 16.20% Ferula asafetida 100 80



41



105



93



79



204 H



121 133



67



60



147



55



40



189



161 175



20 40



60



80



100



120



140



160



180



200



RT: 28.38 AI: 1489 KI: 1490 Vetispirene CAS#: 51196-11-3 MF: C15 H22 FW: 202 MSD LIB#: 1567 CN: spiro(4,5)deca-1,6-diene, 6,10-dimethyl-2-(1-methylethenyl)Synonyms: Source: Vetiver cv. PB, Portugal; 1.00% Vetiveria zizanoides, Rivista Ital EPPOS 54:315(1972) 100



43



160 145



80 91



60 40



105



77



20



53 40



119



65 60



131



202 187



80



100



120



140



160



180



200



RT: 28.43 AI: 1490 KI: 1491 Neryl isobutanoate CAS#: 2345-24-6 MF: C14 H24 O2 FW: 224 MSD LIB#: 1147 CN: propanoic acid, 2-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (Z)Synonyms: neryl isobutyrate Source: Aldrich Chem. ex H. Hills; 1.44% Artemisia absinthum, JEOR 5:239(1993); 0.05% Thymus funkii 100



41



69



80



O



Z



60



93 O



40



80



53



20 40



121 107



60



80



100



120



136 140



154 160



180



200



220



Appendix III: Mass Spectra



485



RT: 28.43 AI: 1490 KI: 1491 Phenyl ethyl 3-methyl butanoate CAS#: 140-26-1 MF: C13 H18 O2 FW: 206 MSD LIB#: 1273 CN: butanoic acid, 3-methyl-, 2-phenylethyl ester Synonyms: phenethyl isovalerate Source: Aldrich Chem. 104



100



O



80



O



60 40



57



20 41 40



65



51



77 85 91



60



80



100



120



140



160



180



200



RT: 28.45 AI: 1491 KI: 1491 Drim-8(12)-ene CAS#: 168113-16-4 MF: C15 H26 FW: 206 MSD LIB#: 631 CN: naphthalene, decahydro-1,1,4a,5-tetramethyl-6-methylene-, (4aR-(4aα, 5α, 8aβ))Synonyms: none Source: ref. cpd. ex P. Weyerstahl 100



41



80



95



81



60



H



137



69



55



109



40



123



191 150



20 40



60



80



100



120



140



163 160



206



177 180



200



RT: 28.45 AI: 1491 KI: 1491 Jasmolactone CAS#: 75253-68-8 MF: C10 H16 O2 FW: 168 MSD LIB#: 957 CN: 2H-pyran-2-one, tetrahydro-6-(3-pentenyl)-, (E)Synonyms: none Source: Firmenich ex Jian-Qin Cu, Kunming; 0.01% Jasminum officinale (absolute), J. Ag. Food Chem. 31:554(1983) 100 41 80



55 O



68



60



O



81



40



108 93



20



150



132 40



60



80



100



120



140



168 160



180



E



Adams: Essential Oil Components by GC/MS



486



RT: 28.47 AI: 1491 KI: 1492 Calamenene CAS#: 143785-42-6 MF: C15 H20 O FW: 216 MSD LIB#: 347 CN: 1,4-ethano-1H-2-benzopyran, 3,4-dihydro-1,3,3,6-tetramethylSynonyms: 1,11-oxidocalamenene Source: ref. cpd. ex P. Weyerstahl 173



100 80



158



60 143



40 43 115



20 40



60



80



100



128



H



O



188 201



120



140



160



180



200



220



RT: 28.47 AI: 1491 KI: 1492 Methyl isoeugenol CAS#: 6379-72-2 MF: C11 H14 O2 FW: 178 MSD LIB#: 352 CN: benzene, 1,2-dimethoxy-4-(1-propenyl)-, (E)Synonyms: trans-methylisoeugenol; 4-trans-propenyl veratrole Source: Calamus oil ex Firmenich ex AF Thomas; 88.80% Melaleuca leucadendra, FFJ 3:43(1988); 85.71% Cinnamomum septentrionale; 20.00% Narcissus poeticus (absolute) 178



100



O-Me O-Me



80 60 40 20 41 40



77



65



51 60



80



163



107



91



E



115 100



135



120



147



140



160



180



RT: 28.49 AI: 1492 KI: 1492 Menthyl lactate CAS#: 000-00-0 MF: C13 H24 O3 FW: 228 MSD LIB#: 1084 CN: not assigned Synonyms: none Source: H & R ex Jian-Qin Cu, Kunming 83



100 80 60



55 41



O



69



40



O



95



20



139 OH



40



60



80



100



120



140



160



180



200



220



240



Appendix III: Mass Spectra



487



RT: 28.49 AI: 1492 KI: 1492 Selinene CAS#: 28624-28-4 MF: C15 H24 FW: 204 MSD LIB#: 594 CN: naphthalene, 2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1-methylethyl)Synonyms: eudesma-4,6-diene Source: ref. cpd. ex Ian Southwell; 18.28% Psidium guajava, FFJ 9:135(1994); 3.69% Psiadia lithospermifolia; 3.67% Alpinia conchigera 161



100 80 41



91



119



81



55



204



105



60 40



133



67



20 40



147



60



80



189



100



120



140



175 160



180



200



RT: 28.51 AI: 1492 KI: 1493 Guaiene CAS#: 88-84-6 MF: C15 H24 FW: 204 MSD LIB#: 758 CN: azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-, (1S-cis)Synonyms: guaia-1(5),7(11)-diene; guaiene Source: guaic wood oil ex R. Stipanovic, TAMU 161



105



100 41 91



80



189



119



60



55



40



204



133



79 67



147



20



175 40



60



80



100



120



140



160



180



200



RT: 28.53 AI: 1493 KI: 1493 Capillene CAS#: 520-74-1 MF: C12 H10 FW: 154 MSD LIB#: 1734 CN: benzene, 2,4-hexadiynylSynonyms: agropyrene, capillen, phenyl-2,4-hexadiyne Source: Santolina rosmarinifolia ex Jesus P. Paul; 53.31% Artemisia pubescens, p. 283, in: Aromatic Plants & Essential Constituents, Peace Book Co., Hong Kong(1993); 0.80% Artemisia waltonii 153



100 80 60 40



51



20



63 40



60



76



115 80



100



120



128



139 140



160



Adams: Essential Oil Components by GC/MS



488



RT: 28.53 AI: 1493 KI: 1493 Muurola-4(14),5-diene CAS#: 54324-03-7 MF: C15 H24 FW: 204 MSD LIB#: 510 CN: naphthalene, 1,2,3,4,4a,5,6,7-octahydro-4-methyl-7-methylene-1-(1-methylethyl)-, (1S,4R,4aR)Synonyms: none Source: Cupressus duclouxiana leaf oil, fraction, ex Larry Cool 161



100



H



80 60



91



40 41 20



55 65 40



60



105 119



81



133



80



100



120



204



147



140



189 160



180



200



RT: 28.53 AI: 1493 KI: 1493 Vetispirene CAS#: 28908-27-2 MF: C15 H22 FW: 202 MSD LIB#: 1566 CN: spiro(4,5)dec-7-ene, 10-methyl-6-methylene-2-(1-methylethylidene)Synonyms: none Source: Vetiver cv. SLA, Portugal; 1.00% Vetiveria zizanoides, Rivista Ital. EPPOS 54:315(1972) 100 80



41



60



105



77



55



40



134



91



67



159 202



145



119



189



20



173 40



60



80



100



120



140



160



180



200



RT: 28.53 AI: 1493 KI: 1493 Zingiberene CAS#: 495-60-3 MF: C15 H24 FW: 204 MSD LIB#: 746 CN: 1,3-cyclohexadiene, 5-(1,5-dimethyl-4-hexenyl)-2-methyl-, (S-(R*,S*))Synonyms: zingiberene Source: distillation of ginger roots (Schilling Co.), RP Adams #5436; 35.56% Zingiber officinale, JEOR 5:465(1993); 4.37% Pimpinella anisum (herb); 1.10% Curcuma xanthorrhiza 100



119



93



H H



80 60 41 69 77



40



105



55



20



133 40



60



80



100



120



147



140



161 160



189 180



204 200



Appendix III: Mass Spectra



489



RT: 28.55 AI: 1493 KI: 1494 Cubebol CAS#: 38230-60-3 MF: C15 H26 O FW: 222 MSD LIB#: 257 CN: 1H-cyclopenta(1,3)cyclopropa(1,2)benzen-3-ol, octahydro-3,7-dimethyl-4-(1-methylethyl)-, (3R(3α,3aβ,3bβ,4β,7α,7aR*))Synonyms: 4-epi-cubebol Source: Ayou oil ex P.Weyerstahl; 3.50% Piper cubeba, Perf Flav. 5:6&27(1980); 0.98% Calendula officinalis; 0.40% Sideritis condensata 100



43



80



93 105



60



119



79



55



40



207



161



69



133



20



179 189



147



218 40



60



80



100



120



140



160



180



200



220



RT: 28.55 AI: 1493 KI: 1494 Decalactone CAS#: 705-86-2 MF: C10 H18 O2 FW: 170 MSD LIB#: 568 CN: 2H-pyran-2-one, tetrahydro-6-pentylSynonyms: 5-decanolide; dihydrojasmin lactone Source: Aldrich Chem.; 11.70% Osmanthus fragrans, Rastit. Resur. 22:243(1986); 0.60% Pinus sibirica; 0.11% Hedychium coronarium 99



100



O



O



80 60 42



71



55



40 20



114



84 40



60



80



100



127 134 141



120



140



152 160



180



RT: 28.55 AI: 1493 KI: 1494 Raspberry ketone, methyl ether CAS#: 104-20-1 MF: C11 H14 O2 FW: 178 MSD LIB#: 1648 CN: 2-butanone, 4-(4-methoxyphenyl)Synonyms: anisylacetone, 2-butanone 13.87 acetoxyanisole, o-; see Guaiacol acetate 18.51 acetoxyelema-1,3-dien-8-ol, 7-; see Elema-1,3-dien-8-ol 39.89 acetoxytoluene, 2-; see Cresol acetate acetoxytoluene, 3-; see Cresol acetate 14.00 acetoxytoluene, α-; see Benzyl acetate 13.96 acetyl formic acid; see Pyruvic acid 2.15 acetyl-2,2-dimethylchromene, 6-; see Desmethoxy encecalin 34.68 acetylanisole, 4-; see Pinocarvone 14.07 acetylbenzene; see Acetophenone 9.99 acetylethylbenzene, p-; see Ethyl acetophenone 19.30 acetyleugenol; see Eugenol acetate 29.70 acetylfuran, 2-furyl methyl ketone, α-; see Acetylfuran 5.19 acor-4-ene(6,11-oxido->; see Italicene ether 30.30 acoradiene, γ-; see Alaskene 29.31 acoradiene,δ; see Alaskene 28.75 adoxal; see Farenal 29.18 agandencidial; see Ugandensidial 53.50 aglaiene; see Copaene 23.49 agropyrene, see Capillene 28.53 ainnamodial; see Ugandensidial 53.50 alloaromadendrene epoxide; see Aromadendrene 34.42 allocimene B; see Ocimene 13.20 allyl 2-aminobenzoate; see Allyl anthranilate 28.89 allyl 3-methylbutanoate; see Allyl isovalerate 5.82 allyl caprate; see Allyl decanoate 27.84 allyl caproate; see Allyl hexanoate 10.72 allyl caprylate; see Allyl octanoate 19.22 allyl cinnamate, trans-; see Allyl cinnamate 30.78 allyl enanthate; see Allyl heptanoate 14.86 allyl pelargonate; see Allyl nonanoate 23.65 allylcatechol methylene ether; see Safrole 19.56 allylguaiacol, 4-; see Eugenol 22.70 allyltetramethoxybenzene; see Elemicin 32.70 ambrox; see Ambroxide 38.81



Adams: Essential Oil Components by GC/MS



aminodicyclohexane; see Dicyclohexyl amine 25.33 amyl alcohol; see Pentanol 2.82 amyl benzoate; see Pentyl benzoate 27.84 amyl butyrate; see Pentyl butanoate 11.08 amyl ethyl ketone; see Octanone 7.19 amyl isobutyrate; see Pentyl isobutanoate 9.62 amyl methyl ketone; see Heptanone 4.74 amyl propionate; see Pentyl propanoate 7.99 amyl salicylate; see Pentyl salicylate 31.85 amyl vinyl ketone; see Pentyl isobutanoate 9.62 amylbenzene; see Benzene 13.73 amylfuran, 2-; see Pentyl furan 7.34 anastil; see Guaiacol 11.00 anethofuran; see Dill ether 15.11 anethole, cis-p-; see Anethole 17.96 angelic acid, isobutyl ester; see Isobutyl angelate 9.45 angelic acid; see Citronellyl tiglate anhydroencecalinol; see Andro encecalinol 35.80 anis alcohol, p-; see Anisyl alcohol 19.24 anisalacetone; see Anisyl methyl ketone 23.75 anisaldehyde, 3-; see Anisaldehyde, 15.57 anisic aldehyde; see Anis aldehyde anisketone; see Anisyl methyl ketone 23.75 anisole, (trans-4-(1-propenyl; see Anethole 19.43 anisole; see Anisole 23.74 anisyl propionate; see Anisyl propanoate 29.26 anisylacetone, 2-butanone 38.95 bisabolene, cis-γ-; see Bisabolene 29.40 bisabolene, trans-γ-; see Bisabolene 30.03 bisabolol oxide II; see Bisabolol oxide B 35.08 bisabolol, dihydro-ar-α-; see Bisabolatrien-7-ol 32.95 brevifolin; see Phloroacetophenone 35.47 buprenene IV; see Cuprenene 30.14 butanal ; see Isovaleraldehyde 2.04



791



butanolide, 4-; see Hydroxybutanoic acid lactone 5.05 buten-2-one, 4-(2-furyl)-3-; see Furfuryl acetone 14.94 butenyl-, (E)-p-1-; see Anisole 23.74 butyl 4-oxovalerate; see Butyl levulinate 17.86 butyl butyrate; see Butyl butanoate 7.58 butyl caproate; see Butyl n-hexanoate 15.19 butyl ethanoate; see Butyl acetate 3.31 butyl ethyl acetic acid; see Ethyl hexanoic acid 12.30 butyl ketone, di-sec-; see Dimethyl-4-heptanone 7.02 butyl laevulinate; see Butyl levulinate 17.86 butyl laurate; see Butyl decanoate 39.86 butyl laurate; see Butyl levulinate 17.86 butyl o-aminobenzoate; see Butyl anthranilate 33.56 butyl phenethyl ketone; see Phenyl heptan-3-one 29.83 butyl valerate; see Butyl pentanoate 11.19 butyl α-methylcrotonate; see Butyl tiglate 12.68 butylacrolein, 3-; see Heptenal 6.27 butylbutyrolactone(γ-); see Octalactone 18.02 butylcarbinol, sec-; see Methyl-1-butanol 2.46 butylene glycol, 2,3-; see Butanediol 3.03 butylphthalide3-; see Butyl phthalide 34.72 butyric acid lactone; see Hydroxybutanoic acid lactone 5.05 butyric acid, propyl ester; see Propyl butanoate 4.91 butyric acid; see Butanoic acid 2.83 butyroin, 5-octanol-4-one; see Octanone 10.23 butyryl lactone; see Hydroxybutanoic acid lactone 5.05 C cadin-4-en-1-ol, 10-β-; see Cubenol 34.63 cadin-4-en-1-ol, 1β,10βH-; see Cubenol 33.95 cadina-1(10),4-diene; see Cadinene 29.72 cadina-1(6),4-diene, 7βH,10βH-; see Cadina-1(6),4diene 27.18 cadinol, tau-; see Cadinol 34.38 cadinol, δ-; see Muurolol 34.61 cajeputene; see Limonene 8.69 cajeputol; see Cineole calamenen-10-α-ol; see Calamenen-10-ol 35.51 calamenen-10-β-ol; see Calamenen-10-ol 35.20 calarene; see Gurjunene 25.95 camazulene; see Chamazulene 37.87 campfieldone; see Apodophylene 36.99 camphenol acetate ; see Nojigiku acetate 17.47 camphogen; see Cymene 8.53 camphol; see Borneol 14.29 campholenaldehyde, α-; see Campholenal 12.46 cantabiline; see Coumarin 46.69 capillen, see Capillene 28.53



792



capric acid, ethyl ester; see Ethyl decanoate 24.40 capric acid; see Decanoic acid 23.02 caprinic acid; see Decanoic acid 23.02 caprinic aldehyde; see Decanal 15.83 caproaldehyde dimethyl acetal; see Hexanal, dimethyl acetal 7.01 caproaldehyde; see Hexanal 3.19 caproic acid, 5-methyl-; see Hexanoic acid 9.03 caproic acid, β-hydroxy-, ethyl ester; see Ethyl 3hydroxy hexanoate 12.40 caproic acid; see Hexanoic acid 6.84 caprolactone, γ-; see Hexalacatone 9.33 caproleic acid; see Decenoic acid 22.80 capryl alcohol; see Octanol 7.60 caprylaldehyde; see Octanal 7.72 caprylene; see Octene 3.06 caprylic acid; see Octanoic acid 14.37 caprylic alcohol; see Octanol 10.11 caprylyl acetate; see Octanol acetate 16.30 carbomethoxyaniline, 2-; see Anthranilate 21.72 carboxystyrene, trans-β-; see Cinnamic acid 26.80 carcacryl acetate; see Carvacrol acetate 23.32 carota-1,4-diene; see Dauca-5,8-diene 27.60 carpic alcohol; see Hexanoic acid 9.03 carvacryl ethyl ether; see Carvacrol, ethyl ether 20.10 carvomenthane; see Menthan-2-one 15.55 carvomenthane; see Menthan-2-one 15.75 carvomenthenol, 4-; see Terpinen-4-ol 14.66 carvomenthenone, 3-; see Piperitone 17.95 caryophylladienol I; see Caryophylla-4(12),8(13)-dien5-β-ol 34.40 caryophyllene epoxide β-; see Caryophyllene oxide 32.16 caryophyllene β-; see Caryophyllene 25.36 caryophyllene, iso-; see Caryophyllene 24.95 caryophyllene, α-; see Humulene 26.82 caryophyllene, β-; see Caryophyllene 25.36 caryphylladienol II; see Caryophylla-4(12),8(13)-dien5-α-ol 34.40 cedr-8(15)-en-9-one; see Cedren-9-one 34.05 cedr-8(15)-ene; see Cedrene 25.42 cedr-8-ene; see Cedrene 25.06 cedran-8-ol, 8-β-; see Cedrol 32.91 cedran-8-ol, acetate, 8-β-; see Cedryl acetate 39.21 cedran-8-ol; see Cedrol 33.59 cedran-9-one, 8-β-; see Cedranone 34.00 cedran-9-α-ol, 8-β-; see Cedranol 36.14 cedran-9-α-ol; see Cedranol 35.68 cedrane, 8,9-epoxide, 8.xi.-; see Cedrene epoxide 31.84 cedrane, 8-α-; see Cedrane 26.62 cedrane, 8-β-; see Cedrane 26.37 cedrelanol; see Cadinol 34.38 cedren-4-one, α-; see Biotone 33.18



Adams: Essential Oil Components by GC/MS



cedrene, 1,7-di-epi-β-; see Funebrene 25.11 cedrene, di-epi-α-, 1,7-; see Funebrene, 24.71 cedrene, di-epi-β-, 1,7-; see Funebrene 25.19 cedrenol acetate; see Cedr-8(15)-en-9-α-ol, acetate 38.26 cedrenol; see Cedr-8(15)-en-9-α-ol 34.83 cedrol acetate; see Cedryl acetate 39.21 celestolide; see Crysolide 37.56 cellusolve acetate; see Ethoxy ethyl acetate 5.03 cellusolve; see Ethoxy ethanol 2.33 cephrol; see Citronellol 16.80 cerulignol; see Eugenol 23.15 cetane; see Hexadecane 32.89 cetanol, cetyl alcohol; see Hexadecanol 43.03 cetene; see Hexadecene 32.44 cetone, α-; see Ionone 27.92 cetyl acetate; see Hexadecyl acetate 47.45 cevadic acid; see Tiglic acid 5.20 champaca camphor; see Guaiol 32.92 champacol; see Guaiol 32.92 chartabomone; see Isotorquatone 41.96 chavicol methyl ether; see Methyl chavicol 15.57 cholestil; see Coumarin 46.69 chromanone, 2-; see Coumarin 23.66 cimmamal; see Cinnamaldehyde 16.53 cimmamein; see Benzyl cinnamate 50.22 cinene; see Limonene 8.69 cinnamic acid cis-, methyl ester; see Methyl cinnamate 20.18 cinnamic acid trans-, benzyl ester; see Benzyl cinnamate 50.22 cinnamic acid, isobutyl ester; see Isobutyl cinnamate 33.80 cinnamic acid, trans-, methyl ester; see Methyl cinnamate 23.58 cinnamyl acetate trans-; see Cinnamyl acetate 26.46 cinnamyl acetate, cis-; see Cinnamyl acetate 24.10 cinnamyl alcohol, cis-; see Cinnamyl alcohol 18.38 cinnamyl alcohol, trans-; see Cinnamyl alcohol 20.36 citral a; see Geranial 18.62 citral b; see Neral 17.32 citral, E-; see Geranial 18.62 citral, Z-; see Neral 17.32 citronellol butanoate; see Citronellyl butanoate 30.05 citronellol isobutyrate; see Citronellol isobutanoate 28.07 citronellyl butyrate; see Citronellyl butanoate 30.05 citronellyl propionate; see Citronellyl propanoate 26.47 citronellyl valerate; see Citronellyl pentanoate 33.82 clorius; see Methyl benzoate 11.07 coerulignol; see Eugenol 23.15 coniferaldehyde; see Cinnamaldhyde 37.78



Appendix IV: Cross Index of Common Names



coniferyl alcohol, cis-; see Coniferyl alcohol 35.48 coniferyl alcohol, trans-; see Coniferyl alcohol 37.98 copaen-11-ol, 2-; see Copaen-11-ol 30.43 cortonaldehyde; see Methyl-2-butenal 2.97 cortonic acid, 2-methyl-, ethyl ester, (E)-; see Ethyl tiglate 5.78 coumarinol, 4-; see Coumarin 40.22 crategine; see Anis aldehyde creosol; 4-methylguaicol; see Cresol 15.27 cresatin; see Cresol acetate 14.00 cresol, 5-(1,5-dimethyl-4-hexenyl), o-; see Xanthorrhizol 38.64 cresol, α-phenyl-, o-; see Hydroxydiphenyl methane 35.75 cresyl caprylate, p-; see Cresol octanoate 39.56 cresyl phenylacetate , m-; see Benzeneacetic acid, 3methylphenyl ester 41.37 crotonaldehyde, 2-methyl-,(E)-; see Tiglic aldehyde 2.58 crotonic acid, 2-methyl-, hexyl ester (E)-; see Hexyl tiglate 21.54 crotonic acid, 2-methyl,methyl ester; see Methyl tiglate 4.28 crotonic acid, cis-2-methyl-2-butenoate; see Isobutyl angelate 9.45 crotonic acid, hexyl ester, hexyl crotonate; see Hexyl (2E)-butanoate 17.49 crotonic acid, trans-2-methyl-; see Tiglic acid 5.20 crotonic acid ; see Butenoic acid, 3methyl-2- 4.60 cubeb camphor; see Cubebol 29.41 cubebol, 4-epi-; see Cubebol 28.55 cumin alcohol; see Cymen-7-ol 19.74 cuminol acetate; see Cymen-7-ol acetate 25.51 cuminol; see Cymen-7-ol 19.74 cuminyl acetate; see Cymen-7-ol acetate 25.51 cumol; see Cumene 5.63 cuprenene 4; see Cuprenene 30.14 cuteazul; see Guaiazulene 39.66 cyclalia; see Hydroxy citronellal 19.60 cyclamal; see Cyclamen aldehyde 27.10 cyclene; see Tricyclene 5.53 cyclogeraniol acetate ; see Cyclogeranyl acetate 28.02 cyclogeraniolene, δ-; see Cyclohexene 2.83 cyclogeraniolene, ε-; see Cyclohexene 3.04 cyclohexadiene, 1,3-; see Phellandrene 7.85 cyclohexanol formate; see Cyclohexyl formate 6.49 cyclohexyl propionate; see Cyclohexyl propanoate 12.79 cyclopentanone, 2-geranyl-; see Apritone 37.04 cyclosia; see Hydroxy citronellal 19.60



793



cyclotrylideneacetone, α-; see Ionone 25.81 cymen-3-ol, p-; see Thymol 19.71 cymol, p-; see Cymene 8.53 cyperenone; see Cyperotundone 36.56 D damascenone, trans-β-; see Damascenone 23.87 dauca-8,11-diene; see Isodaucene 28.83 davanone, cis-hydroxy-; see Davanone-2-ol 37.41 davanone, trans-; see Davanone B 31.46 decadienal, 2-trans, 4-trans-; see Decadienal 20.87 decadienal, 2-trans,4-cis-; see Decadienal 19.86 decalin, cis-; see Naphthalene 11.46 decalin, trans-; see Naphthalene 9.77 decamethylene glycol; see Decanediol 30.75 decamethylenediol; see Decanediol 30.75 decanal, trans-4-; see Decenal 15.60 decanol acetate; see Decyl acetate 24.94 decanolide γ-; see Decalactone 27.35 decanolide, 4-; see Decalactone 27.35 decanolide, 5-; see Decalactone 28.55 decanyl acetate; see Decyl acetate 24.94 decenal, cis-4-; see Decenal 15.48 decenal, trans-2-; see Decenal 18.44 decenol, cis-4-; see Decen-1-ol 18.24 decenol, trans-2-; see Decen-1-ol 18.80 decenol, trans-4-; see Decen-1-ol 18.38 decenyl acetate, trans-2-; see Decenyl acetate 24.96 decyl alcohol, sec-; see Decanol 15.72 decyl alcohol; see Decanol 18.73 decyl propionate; see Decyl propanoate 28.89 decylenic alcohol; see Dec-9-en-1-ol 18.57 dehydroabietinal; see Abietal, dehydro 55.74 dehydroabietyl alcohol; see Abietol, dehydro 58.42 dehydrodeoxybaimuxinol; see Agarofuran 30.79 dehydro-p-cymene; see Cymenene 11.09 delegol T; see Hydroxydiphenyl methane 35.75 deoxybaimuxinol; see Dihydro agarofuran 28.95 desmethylencecalin; see Eupatoriochromene 38.98 dextrocamphroic acid; see Camphoric acid 34.20 diacetone; see Pentanone 3.72 diacetylbenzene,p-; see Acetylacetophenone 26.47 diamyl carbinol; see Undecanol 19.51 diathesin; see Benzenemethanol 18.22 diathesin; see Benzenemethanol 18.22 dicholorobenzene, p-; see Dichlorobenzene 8.18 diethoxy-2-hexene, (E)-1,1-; see Hexenal , Diethyl acetal 11.42 diethoxy-2Z-hexene, 1,1-; see Hexenal , diethyl acetal 10.80 diethyl butanedioate; see Diethyl succinate 14.76



794



diethyl ether; see Ethyl ether 1.63 dihydro citronellyl acetate; see Dihydro citronellol acetate 21.04 dihydro myrcene; see Citronellene 6.15 dihydro-ar-turmerone; see Turmerone 32.70 dihydrocallitrisin; see Callistrisin 46.25 dihydrocarvyl acetate; see Dihydro carveol acetate 20.48 dihydrocitral, 2,3-; see Citronellal 13.58 dihydroeudesmol; see Eudesmol 35.25 dihydroeugenol acetate; see Eugenol acetate 30.30 dihydro-ionone , α, β-; see Ionone 26.08 dihydro-ionone, 7,8-; see Ionone 26.08 dihydrojasmin lactone; see Decalactone 28.55 dihydrotagetone; see Tagetone 9.51 dihydrotoluene, 2,3-; see Cyclohexadiene 3.77 dihydrotoluene, 3,4-; see Cyclohexadiene 3.63 dihydrotoluene ; see Methyl-1,4-cyclohexadiene 3.25 dihydroxydecane, 1,10-; see Decanediol 30.75 dihydroxytoluene, 2,3-; see Catechol 18.20 diisopropyl ketone; see Dimethyl-3-pentanone 3.06 diktaminin; see Dictamine 44.97 dimethoxy geraniol; see Citral 21.90 dimethoxy nerol; see Citral 20.93 dimethoxyphenylmethane; see Benzaldehyde, dimethyl acetal 11.90 dimethoxypsoralen ,5,8-; see Isopimpinellin 54.63 dimethoyx-6,7-furanocoumarin, 5,8-; see Isopimpinellin 54.63 dimethulene; see Chamazulene 37.87 dimethyl acetal decanal; see Decane 23.52 dimethyl salicylate; see Methyl ο-anisate 21.72 dimethyl-2,8-octanediol, 2,6-; see Hydroxy citronellol 22.83 dimethyl-2-butenolide, 4,4-; see Methyl pent-2-enolide 6.21 dimethyl-6-octenal, 3,7-; see Citronellal 13.58 dimethyl-6-octenyl ester, 3,7-; see Citronellyl angelate 35.06 dimethylallyl acetate(1,1); see Buten-2-ol acetate 2.88 dimethylallyl acetate; see Buten-1-ol, 3-methyl-2-, acetate 5.35 dimethylallyl alcohol; see Buten-1-ol 2.85 dimethylbenzenamine, 2,6-; see Dimethyl aniline 14.21 dimethylbenzylcarbinol acetate; see Dimethyl phenethyl acetate 21.04



Adams: Essential Oil Components by GC/MS



dimethylcyclohexene carboxaldehyde; see Vertocitral C 10.61 dimethylcyclohexene carboxaldehyde; see Vertocitral C 11.72 dimethylstyrene, α-3-; see Cymenene 10.82 dimethylstyrene, α-p-; see Cymenene 11.09 dimethylstyrol; see Dimethyl styrene 11.44 dimethylvinylcarbinyl acetate; see Buten-2-ol acetate 2.88 dimethylxanthoxylin, 3,O-; see Acetophenone 36.80 dimethyoxy-β-methyl styrene, (Z)-3,4-; see Methyl isoeugenol 26.78 dimetylethylene glycol; see Butanediol 3.03 dipentene; see Limonene 8.69 diphenyl ketone; see Benzophenone 33.92 diphenyl; see Biphenyl 23.51 dipropyl sulfide; see Disulfide, dipropyl 11.60 dipropylcarbinol; see Heptanol 4.68 dodecanal, trans-2-; see Dodecenal 27.33 dodecanoic acid, butyl ester; see Butyl decanoate 39.86 dodecanolide, 4-; see Dodecalactone 35.85 dodecanolide, 5-; see Dodecalactone 36.91 dodecanone, 2-; see Methyl decyl ketone 24.09 dodecyl alcohol; see Dodecanol 27.52 dragosantol; see Bisabolol 36.17 drim-7-en-11-ol; see Drimenol 39.16 drim-7-ene-11,12-dial; see Polygodial 47.85 drim-8-en-7-one; see Drimenone 40.12 E elleryone; see Zierone 31.86 elsholtzione, dehydro-; see Elsholtzia ketone 20.29 elsholtzione; see Elsholtzia ketone 15.86 enanthaldehyde; see Heptanal 4.98 enanthic alcohol; see Heptanol 6.63 enanthole; see Heptanal 4.98 eperuic acid, methyl ester; see Methyl eperuate 54.15 epiabetinal, 4-; see Abietal 56.44 epicyclocolorenone; see Cyclocolorenone 39.48 epijunicedran-8-one, 6-; see Junicedranone 35.38 epizizanone2-; see Zizanone 35.54 epizonarene, ent-10-; see Epizonarene 28.88 epoxycaryopyllene; see Caryophyllene oxide 32.16 epoxycedrene , α-; see Cedrene epoxide 31.84 epoxyisodihydrocarvone, 1,6-; see Carvone oxide 19.02 epoxymurrolane, 4,10-; see Amorphane 27.91 epoxy-muurolane, 4,10-; see Amorphane 28.05 epoxy-ocimene ; see Epoxy-ocimene 12.72 epoxy-ocimene ; see Epoxy-ocimene 13.10 epoxy-p-menthane, 1,8-; see Cineole eremophila-1(10),11-dien-9-onetone; see Eremophilone 38.02



Appendix IV: Cross Index of Common Names



eremophila-1(10),7(11)-dien-12-ol, 4βH,5α-; see Isovalencenol 40.15 eremophila-9,11-diene, 4βH,5α-; see Aristolochene 28.28 eremophiladiene, 9,11-; see Aristolochene 27.63 esdragol; see Methyl chavicol 15.57 espatulenol; see Spathulenol 31.96 esperone; see Crysolide 37.56 estragole; see Methyl chavicol 15.57 ethanone, 1-(5-methyl-2-furanyl)-; see Furan, 2-acetyl5- methyl- 8.95 ethoxycarbonylbut-1-ene, 4-; see Ethyl pent-4-enoate 4.65 ethyl (Z)-geranate; see Ethyl nerolate 22.48 ethyl 2-methyl-3-pentenoate; see Fruitaleur 6.00 ethyl 2-methylvalerate; see Ethyl 2-methyl pentanoate 5.81 ethyl 3-methylbutnoate; see Ethyl isovalerate 4.04 ethyl 3-methylvalerate; see Ethyl 3-methyl pentanoate 6.34 ethyl 4-oxovalerate; see Ethyl levulinate 9.64 ethyl butyrate; see Ethyl butanoate 3.22 ethyl caprate; see Ethyl decanoate 24.40 ethyl caproate; see Ethyl hexanoate 7.71 ethyl caproic acid,2-; see Ethyl hexanoic acid 12.30 ethyl caprylate; see Ethyl octanoate 15.63 ethyl cis-cinnamte; see Ethyl cinnamate 23.55 ethyl dodecylate; see Ethyl dodecanoate 32.68 ethyl enanthate; see Ethyl heptanoate ethyl ethanoate; see Ethyl acetate 1.80 ethyl glycol acetate; see Ethoxy ethyl acetate 5.03 ethyl glycol; see Ethoxy ethanol 2.33 ethyl heptyl ketone; see Decanone 15.16 ethyl heptylate; see Ethyl heptanoate ethyl heptyne carbonate; see Ethyl-2-octynoate 19.40 ethyl isopentanoate; see Ethyl isovalerate 4.04 ethyl laevulinate; see Ethyl levulinate 9.64 ethyl laurate; see Ethyl dodecanoate 32.68 ethyl myristate; see Ethyl tetradecanoate 40.25 ethyl nonyl ketone; see Dodecanone 24.15 ethyl o-aminobenzoate; see Anthranilate 25.23 ethyl octine carbonate; see Ethyl 2-nonynoate 23.78 ethyl palmitate; see Ethyl hexadecanoate 47.09 ethyl pentyl ketone; see Octanone 7.19 ethyl phenyl ethyl ketone; see Phenyl pentan-3-one 21.80 ethyl phenylacetate; see Benzene acetic acid, ethyl ester 17.69 ethyl propionate; see Ethyl propanoate 2.34 ethyl Pyrazine; see Pyrazine 5.29 ethyl stearate; see Ethyl octadecanoate 53.43 ethyl trans-2-decenoate; see Ethyl-(2E)-decenoate 25.33 ethyl trans-2-hexenoate; see Ethyl hex-(2E)-enoate 9.20 ethyl trans-4-decenoate; see Ethyl-4E-decenoate 23.75 ethyl trans-cinnamate; see Ethyl cinnamate 27.37



795



ethyl valerate; see Ethyl pentanoate 4.96 ethyl vinyl carbinol; see Penten-3-ol 2.16 ethyl α-toluate; see Benzene acetic acid, ethyl ester 17.69 ethyl β-furylpropionate; see Ethyl-3(2-furyl)propanoate 14.85 ethyl-4-butanol, 2-; see Pentanol 3.76 ethylhexyl ethanoate, 2-; see Ethyl hexyl acetate 13.59 ethylprotal; see Vanillin 26.83 see Vanillin 26.83 euasarone; see Asarone 31.78 eucalyptol; see Cineole eucapur; see Cineole eucazulen; see Guaiazulene 39.66 eucol; see Guaiacol acetate 18.51 eudesm-11-en-4-ol, 5β,10α-; see Intermedeol 35.42 eudesm-3-en-11-ol; see Eudesmol 34.91 eudesm-4-en-11-ol; see Eudesm-7(11)-en-4-ol 36.74 eudesm-4-en-3-one, ; see Carissone 44.84 eudesma-3,11-diene; see Selinene 28.74 eudesma-3,7(11)-diene; see Selina-3,7(11)-diene 30.66 eudesma-4(14),11-diene; see Selinene 28.37 eudesma-4(14)-en-11-ol; see Eudesmol 34.79 eudesma-4(14)-en-6α-ol; see Junenol 33.61 eudesma-4,6-diene; see Selinene 28.49 eudesmadiene; see Eudesma-6,11-diene 28.36 eudesmene, β-; see Selinene 28.37 eurogale; see Coumarin 46.69 exaltolide; see Cyclopentadecanolide 41.56 F farnesene, cis-β-; see Farnesene 26.33 farnesene, trans-β-; see Farnesene 26.92 farnesenic acid, trans,trans-; see Farnesoic acid 40.98 farnesol, 2-cis,6-trans-; see Farnesol 36.68 farnesol, cis, cis-; see Farnesol 37.36 farnesol, cis, cis-; see Farnesol 38.30 farnesol, trans, trans-; see Farnesol 37.58 farnesyl acetate, trans, trans-; see Farnesyl acetate 42.01 farnesyl acetate,2-cis-6-trans-; see Farnesyl acetate 41.16 farnesyl acetone, cis, cis-; see Farnesyl acetone 42.54 farnesyl acetone, cis, trans-; see Farnesyl acetone 43.55 farnesyl acetone, trans, cis-; see Farnesyl acetone 43.45 farnesyl acetone, trans, trans-; see Farnesyl acetone 44.37 fenchol, α-; see Fenchol 12.10 fenchol, β-; see Fenchol 12.28 ferruginol, 9-dehydro; see Ferruginol 56.92



796



ferulaldehyde; see Cinnamaldhyde 37.78 fixol; see Hydroxy citronellal 19.60 flomine; see Amyl cinnamaldehyde 35.48 flomine; see Amyl cinnamaldehyde 34.73 folione; see Methyl heptine carbonate 15.60 formylanisole, p-; see Anis aldehyde formylfuran, 2-; see Furfural 3.67 formylphenol, p-; see Hydroxybenzaldehyde 22.65 formylphloroglucinal; see Trihydroxy benzaldehyde 41.06 frambione; see Raspberry ketone 30.67 freesiol; see Heptanol 7.48 frescolate; see Menthyl lactate 27.44 frescolate; see Menthyl lactate 28.05 froggatt ether; see Dihydroagarofuran 28.80 furfuryl alcohol, propionate; see Furfuryl propanate 10.88 furfuryl butyrate; see Furfuryl butanoate 14.50 furfuryl sulfide; see Difurfuryl sulfide 27.10 furfuryl valerate; see Furfuryl pentanoate 18.82 furfurylidenacetone; see Furfuryl acetone 14.94 furo(2,3-b)quinoline, 4-methoxy-; see Dictamine 44.97 furoic acid, 2-; see Methyl 2-furoate 6.90 furoic acid, phenethyl ester,2-; see Phenethyl 2-furoate 37.28 furole, α-; see Furfural 3.67 G gastrodigenin; see Benzenemethanol 21.76 gentanol; see Heptanol 6.63 geraniol 2-methyl butyrate; see Geranyl 2-methyl butanoate 32.93 geraniol acetate; see Geranyl acetate 23.70 geraniol butyrate; see Geranyl butanoate 31.36 geraniol formate; see Geranyl formate 20.11 geraniol isobutanoate; see Geranyl isobutanoate 29.41 geraniol pentanoate; see Geranyl valerate 35.02 geranyl 2-methyl butyrate; see Geranyl 2-methyl butanoate 32.93 geranyl 3-methylbutanoate; see Geranyl isovalerate 33.15 geranyl acetone, trans-; see Geranyl acetone 26.85 geranyl butanoate; see Geranyl butanoate 31.36 geranyl isobutyrate; see Geranyl isobutanoate 29.41 geranyl pentanoate; see Geranyl valerate 35.02 geranylacetone, cis-; see Neryl acetone 26.06 germacra-1(10),4(15),5-triene; see Germacrene D 28.15 germacra-1(10),4,7(11)-triene; see Germacrene B 31.24 germacra-1(10),4-dien-11-ol, 7βH-; see Hedycaryol 30.72 germacra-3,7(11),9-trien-6-one, (E,E)-; see Germacrone 36.48 glycerin; see Glycerol 6.35 glycerol triacetate; see Triacetin 22.31



Adams: Essential Oil Components by GC/MS



glycerol tripropanoate; see Tripropionin 33.00 glycyl alcohol; see Glycerol 6.35 guai-1(5)-en-11-ol; see Guaiol 32.92 guai-11-en-10-ol; see Pogostol 34.89 guaia-1(5),11-diene; see Guaiene 26.20 guaia-1(5),7(11)-diene; see Guaiene 28.51 guaiac acetate; see Guaiol acetate 37.68 guaiastil; see Guaiacol 11.00 guaiyl acetate; see Guaiol acetate 37.68 guaniol; see Geraniol 17.95 gymnomitrene; see Barbatene 26.32 gymnomitrene; see Barbatene 24.92 H heliotropyl acetate; see Piperonyl acetate 28.95 hendecanal; see Undecanal 20.45 hendecane; see Undecane 11.48 hendecanol; see Undecanol 23.19 hendecanone, 2-; see Undecanone 19.90 hendecenal, 9-; see Undec-9E-en-1-al 20.70 hept-2-yl ethanoate; see Heptyl acetate 9.19 hept-4-enol, cis-; see Hepten-1-ol 6.63 heptadienal, trans, trans-2,4-; see Heptadienal 7.99 heptanal, trans-2-; see Heptenal 6.27 heptanolide, 4-; see Heptalactone 13.38 hepten-2-one, trans-3-; see Hepten-2-one 5.71 heptenal, 2,6-dimethyl-5-; see Bergamal 9.67 heptene, 7,7-diethoxy, 3-; see Heptenal , diethyl acetal 15.26 heptenyl acetate, trans-2-; see Heptenyl acetate 11.99 heptyl alcohol, sec-; see Heptanol 4.84 heptyl ethanoate; see Heptyl acetate 12.02 heptyl isobutyrate; see Heptyl isobutanoate 17.84 hepty-δ-valerolacatone , δ-; see Dodecalactone 36.91 heraclin; see Bergaptene 49.10 herniarin, 8-(3-methyl-2-butenyl)-; see Octalactone 18.02 hex-2yl ethanoate; see Acetoxyhexane 6.10 hexadienal, trans-2, trans-4-; see Hexadienal 5.14 hexadienol, trans-trans-2,4-; see Hexadienol 5.29 hexadiynophenone ; see Capillin 34.35 hexahydro-3-butylphthalide; see Phthalide 34.15 hexanolide-1,4; see Hexalacatone 9.33 hexenal, cis-3-; see Hexenal 3.15 hexenal, trans-2-; see Hexenal 3.99 hexenal, trans-3-; see Hexenal 3.10 hexenoic acid, trans-3-; see Hexenoic acid 7.30 hexenol acetate, trans-3-; see Hexenyl acetate 7.84 hexenol, cis-3-; see Hexenol 4.06 hexenol, trans-2-; see Hexenol 4.13



Appendix IV: Cross Index of Common Names



hexenol, trans-3-; see Hexenol 3.96 hexenyl acetate, cis-3-; see Hexenyl acetate 7.93 hexenyl angelate, cis-; see Hexenyl angelate 19.10 hexenyl benzoate, cis-3-; see Hexenyl benzoate 31.48 hexenyl benzoate, trans-2-; see Hexenyl benzoate 32.37 hexenyl butyrate, cis-; see Hexenyl butanoate 15.09 hexenyl butyrate, trans-2-; see Hexenyl butanoate 15.48 hexenyl caproate, cis-3-; see Hexenyl hexanoate 23.65 hexenyl formate, cis-3-; see Hexenyl formate 5.32 hexenyl formate, trans-2-; see Hexenyl formate 5.46 hexenyl isobutyrate ; see Hexenyl isobutanoate 13.30 hexenyl isopentanoate, cis-3-; see Hexenyl isovalerate 17.60 hexenyl isopentanoate ; see Hexenyl isovalerate 17.60 hexenyl phenylacetate, cis-3-; see Hexenyl phenyl acetate 34.16 hexenyl propionate, cis-3-; see Hexenyl propionate 11.30 hexenyl salicylate, cis-3-; see Hexenyl salicylate 35.51 hexenyl tiglate ; see Hexenyl tiglate 21.07 hexenyl tiglate ; see Hexenyl tiglate 20.88 hexon, see Methyl-2-pentanone 2.50 hexyl 3-methyl butanoate; see Hexyl isovalerate 17.59 hexyl alcohol, sec-; see Hexanol 3.14 hexyl butyrate; see Hexyl butanoate 15.40 hexyl caproate; see Hexyl hexanoate 23.83 hexyl caprylate; see Hexyl octanoate 32.12 hexyl isobutyrate; see Hexyl isobutanoate 13.50 hexyl isopentanoate; see Hexyl isovalerate 17.59 hexyl salicylate; see Salicylic acid, hexyl ester 35.75 hexyl-4-butanolide, 4-; see Decalactone 27.35 hexylbutyrolactone γ-; see Decalactone 27.35 hexyl-cinnamaldehdye, trans, 2-; see Cinnamaldehyde 38.51 hexylvalerolactone, δ-; see Undecalactone 32.62 hinokienol, α-; see Muurol-5-en-4-α-ol 31.24 hinokiic acid; see Thujopsenic acid 42.65 humulene 1,2-epoxide; see Humulene epoxide II 33.20 hyderiol; see Heyderiol 59.05 hydrangine; see Coumarin 41.69 hydrocinnamic alcohol; see Hydrocinnamyl alcohol 16.87 hydrocyclopentane; see Cyclopentanol 3.04



797



hydronootkatinol; see Nootkatinol 50.10 hydroquinone dimethyl ether; see Dimethoxybenzene 14.12 hydroxy-3-ethoxybenzaldehyde, 4-; see Vanillin 26.83 hydroxyanisole , o-; see Guaiacol 11.00 hydroxybenzyl alcohol, 3-; see Benzenemethanol(3hydroxy-> 21.92 hydroxycamphene, 6-; see Camphenol 11.98 hydroxycaryophyllene,13-; see Caryophyllene 35.45 hydroxydecane, 3-; see Decanol 15.60 hydroxygermacra-1(10),5-diene ; see Germacrene D-4-ol 31.85 hydroxyindane, 5-; see Indanol 21.90 hydroxyiresane, δ-7(8)-15-; see Drimenol 39.16 hydroxy-p-cresol, α-; see Benzenemethanol 21.76 hydroxy-p-cymene, 8-; see Cymen-8-ol 14.91 hydroxysandaracopimar-15-ene, 8-β-; see Nezukol 51.47 hydroxysesquicineole,(12Z-); see Sesquicineole 39.16 hydroxytoluene, α-; see Benzyl alcohol 8.77 hydroxy-α-terpineol, trans-6-; see Menth-6-en-2,8-diol 23.37 hymecromone; see Coumarin 46.69 hypnone; see Acetophenone 9.99 I imecromone; see Coumarin 46.69 ionol; see Butylated hydroxytoluene 29.43 ionone, trans-α-; see Ionone 25.81 ionone, trans-β-; see Ionone 28.30 irone , α-; see Ionone 29.66 irone, γ-; see Ionone 28.00 isoacetophorone; see Isophorone 12.27 isoamy propionate, see Isoamyl propionate 6.64 isoamyl 2-methyl butanoate; see Isopentyl 2-methyl butanoate 11.49 isoamyl acetate; see Isopentyl acetate 4.40 isoamyl alcohol, sec-; see Methyl-2-butanol 2.10 isoamyl alcohol; see Isopentyl alcohol 2.53 isoamyl caproate; see Isoamyl hexanoate 17.83 isoamyl caprylate; see Isoamyl octanoate 26.42 isoamyl formate; see Isopentyl formate 3.06 isoamyl furylpropionate; see Isoamyl 3-(2-furan) propionate 25.88 isoamyl isovalerate; see Isopentyl isovalerate 11.60 isoamyl laurate; see Isoamyl dodecanoate 41.97 isoamyl methanoate; see Isopentyl formate 3.06 isoamyl n-butyrate; see Isopentyl butanoate 9.72 isoamyl salicylate; see Isopentyl salicylate 30.25 isoamyl trans-cinnamate; see Isoamyl cinnamate 38.21 isoborneol acetate; see Isobornyl acetate 19.48



798



isoborneol propionate; see Isobornyl propanoate 23.88 isobornyl 2-methyl butyrate; see Isobornyl 2-methyl butanoate 29.76 isobornyl butyrate; see Isobornyl n-butanoate 27.72 isobornyl isobutyrate ; see Isobornyl isobutanoate 35.08 isobornyl isobutyrate ; see Isobornyl isobutanoate 33.04 isobornyl isobutyrate ; see Isobornyl isobutanoate 34.56 isobornyl isobutyrate ; see Isobornyl isobutanoate 35.75 isobornyl isobutyrate ; see Isobornyl isobutanoate 43.56 isobutenylcarbinol; see Buten-1-ol 2.45 isobutyl alcohol; see Isobutanol 2.00 isobutyl caproate; see Isobutyl hexanoate 13.62 isobutyl crotonate; see Isobutyl(2E)-butenoate 7.62 isobutyl ethanoate; see Isobutyl acetate 2.81 isobutyl methanoate; see Isobutyl formate 2.14 isobutyl o-hydroyxbenzoate; see Isobutyl salicylate 25.59 isobutyl propyl ketone; see Heptanone 5.46 isobutyl-3-methoxypyrazine, 2-; see Pyrazine 14.91 isobutylmethylcarbinol; see Pentanol 2.66 isobutylthiazole,2-; see Thiazole 8.89 isobutylα-toluate; see Isobutyl phenylacetate 24.01 isobutyric acid, isobutyl ester; see Isobutyl isobutyrate 5.18 isobutyric acid, isopropyl ester; see Isopropyl isobutyrate 3.08 isobutyrone; see Dimethyl-3-pentanone 3.06 isocaproic acid; see Pentanoic acid 5.89 isocarveol, trans-; see Mentha-1(7),8-dien-2-ol 15.24 isocaryophyllene; see Caryophyllene 24.95 isocedrenone; see Cedren-9-one 34.05 isocedrol, 6-; see Cedrol 33.59 isochinolin; see Isoquinoline 17.97 isodextropimaraldehyde; see Sandaracopimarinal 53.06 isodihydrolavandulyl aldehyde; see Isopropyl-5-methyl(2E)-hexenal 11.66 isoelemicin, cis-; see Isoelemicin 31.62 isoenanthic acid; see Hexanoic acid 9.03 isoeugenol acetate, trans-; see Isoeugenol acetate 33.46 isoeugenol, cis-; see Isoeugenol 24.90 isoeugenol, trans-; see Isoeugenol 26.67 isofuranogermacrene; see Curzerene 28.79 isogermafurene; see Curzerene 28.79 isohexyl 2-methylbutyrate; see Butanoic acid, 2-methyl4-methylpentyl ester 15.66 isokaurene; see Kaur-15-ene 47.25



Adams: Essential Oil Components by GC/MS



isomethyleugenol, cis-; see Methyl isoeugenol 26.78 isomethyl-α-ionone; see Ionone isomyristicin, trans-; see Isomyristicin 33.52 isoneral; see Isocitral 14.06 isopatchoulenone; see Cyperotundone 36.56 isopentanal; see Isovaleraldehyde 2.04 isopentenylcoumarin, 7-methoxy-8-; see Octalactone 18.02 isopentyl 2-methyl butyrate; see Isopentyl 2-methyl butanoate 11.49 isopentyl acetoacetate; see Isoamyl acetoacetate 14.72 isopentyl alcohol, 3-; see Buten-1-ol 2.45 isopentyl benzoate; see Isoamyl benzoate 26.03 isopentyl benzyl ether; see Isoamyl benzyl ether 20.64 isopentyl butyrate; see Isopentyl butanoate 9.72 isopentyl dodecanoate; see Isoamyl dodecanoate 41.97 isopentyl ethanoate; see Isopentyl acetate 4.40 isopentyl geranate; see Isoamyl geranate 34.85 isopentyl hexenoate; see Isoamyl hexanoate 17.83 isopentyl isobutyrate; see Isoamyl isobutyrate 8.05 isopentyl laurate; see Isoamyl dodecanoate 41.97 isopentyl methanoate; see Isopentyl formate 3.06 isopentyl nerolate; see Isoamyl nerolate 33.00 isopentyl nonanoate; see Isoamyl nonanoate 30.59 isopentyl propanoate; see Isoamyl propionate 6.64 isopenyl octanoate; see Isoamyl octanoate 26.42 isopimara-7,15-dien-18-ol; see Isopimarol 56.77 isopimaradien-18-ol, 8(14),15-; see Sandaracopimarinol 55.58 isopimarinol; see Isopimarol 56.77 isopimarinol; see Sandaracopimarinol 55.58 isopinocamphone; see Pinocamphone 14.57 isopropenyl-2-methylcyclohexanone, 5-; see Dihydro carvone 15.41 isopropenylangelicin 5'-; see Oroselone 52.08 isopropenyltoluene, 4-; see Cymenene 11.09 isopropenyltoluene, m-; see Cymenene 10.82 isopropyl acetone, see Methyl-2-pentanone 2.50 isopropyl butyrate; see Isopropyl butanoate 3.81 isopropyl ketone; see Dimethyl-3-pentanone 3.06 isopropyl myristate; see Isopropyl tetradecanoate 41.42 isopropyl palmitate; see Isopropyl hexadecanoate 48.09 isopropylbenzene; see Cumene 5.63 isopropylresorcinol dimethyl ether, 5-; see Benzene 24.37 isopropyltoluene, p-; see Cymene 8.53 isopropyltropolon, 4-; see Nezukone 26.12 isoterpinene; see Terpinolene 10.98 isoterpinolene; see Mentha-2,4(8)-diene 10.94 isovaleral; see Isovaleraldehyde 2.04 isovaleric acid geranyl ester; see Geranyl isovalerate 33.15 isovaleric acid, 2-methylbutyl ester; see Methyl butyl isovalerate 11.65 isovaleric acid, 3-hexenyl ester, (Z)-; see Hexenyl 3methyl butanoate 17.22



Appendix IV: Cross Index of Common Names



J jasmal; see Amyl cinnamaldehyde 35.48 jasmal; see Amyl cinnamaldehyde 34.73 jasmatone; see Dihydroisojasmone 21.97 jasminaldehyde; see Amyl cinnamaldehyde 34.73 jasmone, trans-; see Jasmone 24.19 jatamansone; see Valeranone 35.74 juniper camphor, acetate; see Eudesm-7(11)-en-4-ol, acetate 41.80 juniper camphor; see Eudesm-7(11)-en-4-ol 36.74 juniperic acid lactone; see Cyclohexadecanolide 45.07 K kaur-15-ene, ; see Isohibaene 45.05 kautschin; see Limonene 8.69 kessazulen; see Guaiazulene 39.66 ketoisophorone; see Isophorone 13.23 ketole; see Indole 19.76 ketone, methyl 2-thiazolyl; see Thiazole 8.32 ketone, methyl 2-thienyl; see Acetylthiophene 10.97 ketone, methyl pyrazinyl; see Pyrazine 8.41 khusenic acid; see Vetivenic acid 40.80 Kodaflex triacetin; see Triacetin 22.31 kryptomeren; see Kaur-15-ene 47.25 kusunol; see Valerianol 35.07 L labd-8(20)-en-15-oic acid, methyl ester, 5β,9βH,10α-; see Methyl eperuate 54.15 labda-12,14-dien-8-ol; see Abienol 51.98 labda-8(20),14-dien-13-ol, (13S)-; see Manool 49.20 labda-8(20),14-dien-13-ol,(13R)-; see Manool 49.11 labda-8(20),14-diene-13,19-diol; see Torulosol 58.21 labdanolic acid, methyl ester; see Methyl labdanolate 58.80 lactic acid, butyl ester, butyrate; see Butyl butyryl lactate 22.57 lauraldehyde; see Dodecanal 24.95 lauric acid, butyl ester; see Butyl dodecanoate 39.92 lauric acid; see Dodecanoic acid 31.47 lauric aldehyde; see Dodecanal 24.95 lauryl acetate; see Dodecyl acetate 33.17 lauryl alcohol; see Dodecyl acetate 33.17 leaf acetal; see Leaf alcohol, ethyl acetal 11.77 leaf alcohol; see Hexenol 4.06 lebaicone; see Sabina ketone 12.25 ledene; see Viridifolene 28.68 lemonol; see Geraniol 17.95 leucoline; see Isoquinoline 17.97 ligustrazine; see Pyrazine 10.86 lilyal; see Lilial 29.93 lilyl aldehyde; see Hydroxy citronellal 19.60 linalool acetate; see Linalyl acetate 18.16



799



linarodin; see Acetophenone